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| phosphitesSummarySummary: Inorganic salts or organic esters of phosphorous acid that contain the (3-)PO3 radical. (From Grant & Hackh's Chemical Dictionary, 5th ed) Top Publications
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Synthesis, antiviral and antifungal bioactivity of 2-cyano-acrylate derivatives containing phosphonyl moietiesYin Pu Lv
Center for Research and Development of Fine Chemicals, Guizhou University, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guiyang, 550025, PR China
Molecules 12:965-78. 2007..were synthesized by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylates with dialkyl phosphites. The structures of the new compounds were characterized by elemental analyses, IR, 1H-, 13C- and 31P-NMR ..
Environmentally benign beta-stereoselective glycosidations of glycosyl phosphites using a reusable heterogeneous solid acid, montmorillonite K-10Hideyuki Nagai
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
Carbohydr Res 340:337-53. 2005Environmentally benign and stereoselective beta-glycosidations of glycopyranosyl phosphites and alcohols using a reusable heterogeneous solid acid, montmorillonite K-10, as an activator have been developed...
Ethyl(methyl)dioxirane as an efficient reagent for the oxidation of nucleoside phosphites into phosphates under nonbasic anhydrous conditionsM Kataoka
Laboratory of Bioorganic Chemistry, Graduate School of Human Informatics, Nagoya University, Chikusa, Nagoya 464-8601, Japan
Org Lett 3:815-8. 2001A convenient method for the oxidation of nucleoside phosphites into phosphates under nonbasic and nonaqueous conditions using commercially available ethyl(methyl)dioxirane has been developed...
Mechanism and applications of phosphite dehydrogenaseHeather A Relyea
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 S. Matthews Ave, Urbana, IL 61801, USA
Bioorg Chem 33:171-89. 2005..The potential of the enzyme as a NAD(P)H cofactor regeneration system is discussed as well as efforts to engineer the cofactor specificity of the protein...
Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halidesDmitri Gelman
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA
Org Lett 5:2315-8. 2003..A variety of sterically hindered and/or functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields. [reaction: see text]..
Heterogeneous catalytic oxidation of hypophosphite by H2O2: pH effectC C Hung
Department of Chemical Engineering, National Cheng Kung University, Tainan City 701, Chinese Taiwan
Water Sci Technol 55:89-93. 2007..0 than that at pH 2.5. We conclude that it is a major heterogeneous catalytic oxidation by our novel iron oxide catalyst to oxidise HP at pH 4.0. Also, B1 could be a useful and potential catalyst for the treatment of HP wastewater...
Synthesis of new chiral monodentate phosphite ligands and their use in catalytic asymmetric hydrogenationZihao Hua
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA
Org Lett 5:3831-4. 2003..The new chiral ligand system is suitable to create libraries and possesses fine-tuning capability...
Microbial metabolism of reduced phosphorus compoundsAndrea K White
Department of Biological Sciences, California State University, Chico, California 95928 0515, USA
Annu Rev Microbiol 61:379-400. 2007....
Tautomerism and hydrogen bonding in guaninium phosphite and guaninium phosphate saltsEl Eulmi Bendeif
Laboratoire de Cristallographie et Modélisation des Matériaux Minéraux et Biologiques LCM3B CNRS UMR 7036, Universite Henri Poincare, Nancy 1, Faculte des Sciences, Vandoeuvre les Nancy Cedex, France
Acta Crystallogr B 63:448-58. 2007..An investigation of the hydrogen-bond network in these guaninium salts reveals the existence of two ketoamine tautomers, the N9H form and an N7H form...
Heteropolymolybdates of phosphate, phosphonate, and phosphite functionalized by glycineUlrich Kortz
School of Engineering and Science, International University Bremen, 28725 Bremen, Germany
Inorg Chem 42:1135-9. 2003..NMR studies show that the solid state structures of the title compounds are preserved in solution...
Synthesis of 1-(N-ethoxycarbonylamino)alkylphosphonic monoestersH Liu
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, China
Amino Acids 29:241-3. 2005..A series of 1-(N-ethoxycarbonylamino)alkylphosphonic monoesters were synthesized via three-component Mannich-type condensation of ethyl carbamate, aldehydes and dichlorophosphites in benzene, followed by hydrolysis...
Synthesis of beta-substituted alpha-amino acids with use of iridium-catalyzed asymmetric allylic substitutionTakatoshi Kanayama
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan
J Org Chem 68:6197-201. 2003..In addition, both diastereomers of the branch products were synthesized stereoselectively by simply switching the base employed. These methods were also applied to the asymmetric synthesis of quaternary alpha-amino acids...
Organocatalytic asymmetric direct phosphonylation of alpha,beta-unsaturated aldehydes: mechanism, scope, and application in synthesisEddy Maerten
Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK 8000, Aarhus C, Denmark
J Org Chem 72:8893-903. 2007..DFT calculations have been applied to explain the approach of the phosphite to the reactive carbon atom in the iminium intermediate in order to account for the observed absolute enantioselectivity in the reaction...
Enantioselective metallophosphite-catalyzed C-acylation of nitronesMary R Garrett
Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA
J Am Chem Soc 129:12944-5. 2007
Stereochemical features making deoxycholic acid derived tropos biphenylphosphites efficient chiral ligands for rhodium: the asymmetric hydrogenation of dimethylitaconate as a case studyAnna Iuliano
Dipartimento di Chimica e Chimica Industriale, Universita di Pisa, Via Risorgimento 35, 56126 Pisa, Italy
J Org Chem 72:8472-7. 2007..atropoisomeric binaphthyl analogues, together with NMR and CD measurements on the rhodium complexes of some phosphites, allowed us to shed light on the nature of the active catalytic species and on the asymmetric induction process ..
Femtosecond pulse shaping adds a new dimension to mass spectrometryIgor Pastirk
Biophotonic Solutions, Inc, Okemos, Michigan 48864, USA
Appl Opt 46:4041-5. 2007....
New biphenol-based, fine-tunable monodentate phosphoramidite ligands for catalytic asymmetric transformationsZihao Hua
Department of Chemistry, Stony Brook University, Stony Brook, NY 11794-3400, USA
Proc Natl Acad Sci U S A 101:5411-6. 2004..The fine-tuning capability of these ligands plays a significant role in achieving high enantioselectivity in the asymmetric hydroformylation of allyl cyanide and the conjugate addition of diethylzinc to cycloalkenones...
Calix[4]arene alpha-aminophosphonic acids: asymmetric synthesis and enantioselective inhibition of an alkaline phosphataseSergiy Cherenok
The Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska, 5, 02094, Kyiv-94, Ukraine
Org Lett 8:549-52. 2006..alpha-aminophosphonic acids were obtained through diastereoselective Pudovik-type addition of sodium ethyl phosphites to the chiral calixarene imines, removal of chiral auxiliary groups, and mild dealkylation of phosphonate ..
Two C-P lyase operons in Pseudomonas stutzeri and their roles in the oxidation of phosphonates, phosphite, and hypophosphiteAndrea K White
Department of Microbiology, University of Illinois, B103 Chemical and Life Sciences Laboratory, 601 S Goodwin Ave, Urbana, IL 61801, USA
J Bacteriol 186:4730-9. 2004..The substrate ranges of both C-P lyases are limited, as growth on other phosphonate compounds, including glyphosate and phenylphosphonate, was not observed...
Rates and equilibria of the reactions of tertiary phosphanes and phosphites with benzhydrylium ionsBernhard Kempf
, Butenandtstrasse 5-13 (Haus F, , Germany
Chemistry 11:917-27. 2005The kinetics of the reactions of benzhydrylium ions and quinone methides with eight tertiary phosphanes and two phosphites were investigated photometrically...
How to get the most out of two phosphorus chemistries. Studies on H-phosphonatesJacek Stawinski
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-10691 Stockholm, Sweden
Acc Chem Res 35:952-60. 2002..In this Account, the authors' studies on the development of a comprehensive H-phosphonate methodology and the underlying chemistry for the preparation of biologically important phosphate esters and their analogues are briefly discussed...
Isolation and biochemical characterization of hypophosphite/2-oxoglutarate dioxygenase. A novel phosphorus-oxidizing enzyme from Psuedomonas stutzeri WM88Andrea K White
Department of Microbiology, University of Illinois, Urbana, Illinois 61801, USA
J Biol Chem 277:38262-71. 2002..The substrate analog inhibitors, formate and nitrate, significantly reduce HtxA activity...
Click-connected ligand scaffolds: macrocyclic chelates for asymmetric hydrogenationQing Zhang
Department of Chemistry, University of Nebraska Lincoln, Lincoln, Nebraska 68588 0304, USA
Org Lett 10:545-8. 2008..Enantioselectivity as high as 97% ee is obtained using these click ligands in rhodium-catalyzed asymmetric hydrogenation. Control experiments and spectroscopic data suggest that a 16-membered P,P-macrocyclic Rh(I) chelate is formed...
Electronic structure of mononuclear bis(1,2-diaryl-1,2-ethylenedithiolato)iron complexes containing a fifth cyanide or phosphite ligand: a combined experimental and computational studyApurba K Patra
, Stiftstrasse 34-36, , Germany
Inorg Chem 45:7877-90. 2006..The electronic structures of 1 and 1(ox) have been established by density functional theoretical calculations: [Fe(II)(1L*)2(CN)]1- (SFe = 0, St = 0) and [Fe(III)(1L*)2(CN)]0 (SFe = 3/2, St = 1/2)...
Parallel synthesis and screening of polymer-supported phosphorus-stereogenic aminophosphane-phosphite and -phosphinite ligandsRené den Heeten
van t Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands
Angew Chem Int Ed Engl 47:6602-5. 2008
TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroborationShin A Moteki
Department of Chemistry and Nebraska Center for Materials and Nanoscience, University of Nebraska-Lincoln, 68588, USA
Org Lett 8:3097-100. 2006..Rhodium(I) chloride and tetrafluoroborate catalyst precursors give comparable results. Pinacolborane is superior to catecholborane in these reactions...
Ambient temperature synthesis of high enantiopurity N-protected peptidyl ketones by peptidyl thiol ester-boronic acid cross-couplingHao Yang
Department of Chemistry, Emory University, 1515 Dickey Drive NE, Atlanta, Georgia 30322, USA
J Am Chem Soc 129:1132-40. 2007..The peptidyl ketone synthesis proceeds at room temperature under nonbasic conditions and demonstrates a high tolerance to functionality...
Chiral pyranoside phosphite-oxazolines: a new class of ligand for asymmetric catalytic hydrogenation of alkenesMontserrat Diéguez
Departament de Quimica Fisica i Inorganica, Universitat Rovira i Virgili, Campus Sescelades, C Marcel li Domingo, s n 43007 Tarragona, Spain
J Am Chem Soc 130:7208-9. 2008..So, this is an exceptional ligand class that competes favorably with a few other ligand series that also provide high ee values for tri- and disubstituted substrate types...
Chiral phosphite-oxazolines: a new class of ligands for asymmetric Heck reactionsYvette Mata
, Universitat Rovira i Virgili, C/Marcel li Domingo, s/n, 43007 Tarragona, Spain
Org Lett 7:5597-9. 2005....
Synthesis of sulfonium sulfate analogues of disaccharides and their conversion to chain-extended homologues of salacinol: new glycosidase inhibitorsBlair D Johnston
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6
J Org Chem 71:1111-8. 2006....
Asymmetric synthesis of N-protected chiral 1-aminoalkylphosphonic acids and synthesis of side chain-functionalized depsiphosphonopeptidesHan Liu
Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
J Pept Sci 12:337-40. 2006..Side chain-functionalized depsiphosphonopeptides were also prepared in satisfactory yields directly from one-pot reactions of benzyl carbamate, aldehydes, and diethyl (R,R)-2-chloro-1,3,2-dioxaphospholane-4,5-dicarboxylate...
Modular phosphite-oxazoline/oxazine ligand library for asymmetric pd-catalyzed allylic substitution reactions: scope and limitations-origin of enantioselectivityMontserrat Diéguez
Departament de Quimica Fisica i Inorganica, Universitat Rovira i Virgili Campus Sescelades, C Marcel li Domingo, s n 43007 Tarragona, Spain
Chemistry 14:3653-69. 2008..It also indicates that the nucleophilic attack takes place predominantly at the allylic terminal carbon atom located trans to the phosphite moiety...
Solid-phase parallel synthesis of phosphite ligandsBert H G Swennenhuis
Van t Hoff Institute of Molecular Sciences, University of Amsterdam, The Netherlands
Org Lett 10:989-92. 2008Various routes for the synthesis of polymer-bound phosphites and phosphoramidites have been investigated...
Effect of amino substituents on the stereochemical outcome of the photo-Arbuzov rearrangements of 1-arylethyl phosphorodiamiditesWorawan Bhanthumnavin
Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, USA
J Org Chem 70:4643-51. 2005..formed by carbon-oxygen bond scission (Scheme 1), which are somewhat longer lived than those from the analogous phosphites 5 and 6, is proposed...
Umpolung catalysts: comparative assessments on reactivitiesBernd Goldfuss
Institut fur Organische Chemie, Greinstrasse 4, 50939, Koln, Germany
J Mol Model 12:591-5. 2006..The nucleophilic carbene, N-methylthiazol-2-ylidene, is the strongest umpolung catalyst, while the phosphite is about as active as cyanide...
Highly enantioselective Rh-catalyzed hydrogenation based on phosphine-phosphite ligands derived from carbohydratesO Pàmies
Departament de Quimica Fisica i Inorganica, Universitat Rovira i Virgili, Pl Imperial Tarraco 1, 43005 Tarragona, Spain
J Org Chem 66:8364-9. 2001....
Synthesis of biologically active amines via rhodium-bisphosphite-catalyzed hydroaminomethylationJohn R Briggs
Chemical Sciences, The Dow Chemical Company, Midland, Michigan 48674, USA
Org Lett 7:4795-8. 2005..This catalyst system was successfully applied in the synthesis of two biologically active tertiary amines, ibutilide and aripiprazole...
Synthesis of solution-phase phosphoramidite and phosphite ligand libraries and their in situ screening in the rhodium-catalyzed asymmetric addition of arylboronic acidsRichard B C Jagt
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
J Comb Chem 9:407-14. 2007..It is shown that the described methodology results in the straightforward discovery of leads for highly efficient enantioselective catalysts...
Chiral diphosphites derived from D-glucose: new highly modular ligands for the asymmetric catalytic hydrogenationMontserrat Diéguez
Departament de Quimica Fisica i Inorganica, Universitat Rovira i Virgili, Pl Imperial Tarraco 1, 43005 Tarragona, Spain
J Org Chem 67:3796-801. 2002..Moreover, the presence of bulky substituents at the ortho-positions of the biaryl diphosphite moieties has a positive effect on enantioselectivity...
Asymmetric hydroformylation with highly crosslinked polystyrene-supported (R,S)-BINAPHOS-Rh(I) complexes: the effect of immobilization positionFumitoshi Shibahara
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, Hongo Bunkyo-ku, Japan
Bioorg Med Chem Lett 12:1825-7. 2002..Using its Rh(I) complex, asymmetric hydroformylation of olefins proceeded with higher enantioselectivity in some cases compared to the conventional polymer-supported 1c...
The htx and ptx operons of Pseudomonas stutzeri WM88 are new members of the pho regulonAndrea K White
Department of Microbiology, University of Illinois, B103 Chemical and Life Sciences Laboratory, 601 S Goodwin Ave, Urbana, IL 61801, USA
J Bacteriol 186:5876-82. 2004..The putative LysR-type regulator encoded by ptxE has no apparent role in the expression of the htx and ptx operons, as no effect was observed on the level of induction of either operon in a DeltaptxE mutant...
Phosphonate analogues of alpha-ketoglutarate inhibit the activity of the alpha-ketoglutarate dehydrogenase complex isolated from brain and in cultured cellsVictoria I Bunik
School of Bioinformatics and Bioengineering and Belozersky Institute of Physico Chemical Biology, Moscow State University, Moscow 119992, Russian Federation
Biochemistry 44:10552-61. 2005....
Thermal synthesis of nucleoside H-phosphonates under mild conditionsR M De Graaf
Evolutionary Biology Research Group, Faculty of Science, University of Nijmegen, 6500 GL Nijmegen, The Netherlands
Orig Life Evol Biosph 35:1-10. 2005..These results confirm earlier suggestions that nucleoside H-phosphonates and their possible condensation products may have been produced on the primitive earth more easily than nucleotides...
Does phosphoryl protonation occurs in aqueous phosphoesters solutionsL Azema
Laboratoire de Synthèse et Physico Chimie de Molécules d Intérêt Biologique, UMR CNRS 5068, Universite Paul Sabatier, 118 route de Narbonne 31062 Toulouse cedex 4, France
Spectrochim Acta A Mol Biomol Spectrosc 62:287-92. 2005..This finding will gain to be further explored on more complex molecules like phospholipids, nucleic acids and proteins...
Formation of 4,4'-dimethoxytrityl-C-phosphonate oligonucleotidesDaniel C Capaldi
Isis Pharmaceuticals, Inc, 2292 Faraday Avenue, Carlsbad, CA 92008, USA
Bioorg Med Chem Lett 14:4683-90. 2004..DMTr-C-phosphonate derivatives are not detected when optimized sulfurization conditions are employed...
Multidimensional analytical method based on binary phase shaping of femtosecond pulsesI Pastirk
J Phys Chem A 109:2413-6. 2005..Experimental results on dimethyl phosphite and pyridine illustrate the new approach toward the real-time accurate detection and identification of chemical compounds including isomers...
Electron-rich heteroaroylphosphonates and their reaction with trimethyl phosphiteD Vaughan Griffiths
School of Biological and Chemical Sciences, Queen Mary, University of London, Mile End Road, London, EnglandE1 4NS
Org Biomol Chem 6:577-85. 2008..The latter process appears to be suppressed by a substituent at the 5-position of the furan ring, the resulting ylidic phosphonates being a rare example of an efficient intermolecular trapping of a furan-2-yl carbene...
Integration of chloroplast nucleic acid metabolism into the phosphate deprivation response in Chlamydomonas reinhardtiiShlomit Yehudai Resheff
Boyce Thompson Institute for Plant Research, Cornell University, Ithaca, New York 14853, USA
Plant Cell 19:1023-38. 2007..This unusual phenomenon, which is phosphite- and PSR1-insensitive, may have evolved as a result of the polyploid nature of cpDNA and the requirement of P for cpRNA degradation by PNPase...
Membrane lipid alteration during phosphate starvation is regulated by phosphate signaling and auxin/cytokinin cross-talkKoichi Kobayashi
Department of Bioscience, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 B 14 Nagatsuta cho, Midori ku, Yokohama 226 8501, Japan
Plant J 47:238-48. 2006..These results indicate that the observed global change in plant membranes during Pi starvation is not caused by Pi-starvation induced damage in plant cells but rather is strictly regulated by Pi signaling and auxin/cytokinin cross-talk...
Arabidopsis pdr2 reveals a phosphate-sensitive checkpoint in root developmentCarla A Ticconi
Department of Vegetable Crops, University of California-Davis, One Shields Avenue, Davis, CA 95616, USA
Plant J 37:801-14. 2004....
Phosphite, an analog of phosphate, suppresses the coordinated expression of genes under phosphate starvationDeepa K Varadarajan
Department of Horticulture and Landscape Architecture, Purdue University, West Lafayette, Indiana 47907-1165, USA
Plant Physiol 129:1232-40. 2002..Synchronized suppression of multiple Pi starvation-induced genes by Phi points to its action on the early molecular events, probably signal transduction, in Pi starvation response...
Attenuation of phosphate starvation responses by phosphite in ArabidopsisC A Ticconi
Department of Vegetable Crops, University of California, One Shields Avenue, Davis, CA 95616, USA
Plant Physiol 127:963-72. 2001..Thus, the use of Phi may allow further dissection of phosphate signaling by genetic selection for constitutive phosphate starvation response mutants on media containing organophosphates as the only source of phosphorus...
Biaryl phosphites: new efficient adaptative ligands for Pd-catalyzed asymmetric allylic substitution reactionsMontserrat Diéguez
Departament de Quimica Fisica i Inorganica, Universitat Rovira i Virgili, C Marcel li Domingo s n, 43007 Tarragona, Spain
Acc Chem Res 43:312-22. 2010..This Account discusses the application of homo- and heterodonor biaryl-containing phosphites as new, versatile, and highly effective ligands in the Pd-catalyzed asymmetric allylic substitution of several ..
Chiral diphosphine and monodentate phosphorus ligands on a spiro scaffold for transition-metal-catalyzed asymmetric reactionsJian Hua Xie
State Key Laboratory and Institute of Elemento Organic Chemistry, Nankai University, Tianjin 300071, China
Acc Chem Res 41:581-93. 2008..and SFDP with a 9,9'-spirobifluorene backbone, and the spiro monophosphorus ligands including phosphoramidites, phosphites, phosphonites, and phospholane with a 1,1'-spirobiindane backbone were synthesized in good yields from ..
Synthesis of phosphites and phosphates of neuraminic acid and their glycosyl donor properties--convenient synthesis of GM3T J Martin
Fakultat Chemie, Universitat Konstanz, Germany
Glycoconj J 10:16-25. 1993..readily available N-acetylneuraminic acid, derivative 1 with phosphochloridites 2a-f and Huenigs' base sialyl phosphites 3a-f were prepared and isolated in high yields...
Asymmetric hydrophosphylation of chiral N-phosphonyl imines provides an efficient approach to chiral α-amino phosphonatesParminder Kaur
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409 1061, USA
Chem Biol Drug Des 76:314-9. 2010Chiral N-phosphonylimines were found to react with lithium phosphites to provide various substituted chiral α-amino phosphonates in excellent yields (94-97%) and diastereoselectivities (93:7-99:1)...
Probing substituent effects on the activation of H(2) by phosphorus and boron frustrated Lewis pairsRebecca C Neu
Department of Chemistry, University of Toronto, 80 St George St Toronto, Ontario, CanadaM5S 3H6
Dalton Trans 39:4285-94. 2010..The phosphites (RO)(3)P R = Me, Ph form classical Lewis acid-base adducts of the formula (RO)(3)PB(C(6)F(5))(3) R = Me ; R = Ph ..
Phosphoramidites are efficient, green organocatalysts for the Michael reaction. Mechanistic insights into the phosphorus-catalyzed Michael reaction of alkynones and implications for asymmetric catalysisRobert B Grossman
Department of Chemistry, University of Kentucky, Lexington, Kentucky 40506 0055, USA
J Org Chem 68:871-4. 2003Hexamethylphosphorous triamide (HMPT) and other phosphoramidites and phosphites have been found to be efficient catalysts for the Michael reaction of alkenones and alkynones with malonates, alpha-cyano esters, beta-keto esters, and nitro ..
Electron spin resonance study of phosphorus-nitroxides from 1,3-additions of silicon-phosphorus reagents to nitronesD Lawrence Haire
Department of Clinical Studies, Ontario Veterinary College, University of Guelph, Guelph, ON, N1G 2W1, Canada
Magn Reson Chem 42:835-43. 2004..Specifically, the reaction sequence involves the novel 1,3-addition of trimethylsilyl phosphites (e.g. diethyl) or trimethylsilyl phosphines (e.g. diphenyl) to aldo-nitrones [e.g...
Organic reactions in water: a distinct novel approach for an efficient synthesis of alpha-amino phosphonates starting directly from nitro compoundsBiswanath Das
Organic Chemistry Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
J Org Chem 74:8400-2. 2009..discovered through three-component reaction of nitro compounds, aldehydes, or ketones and dialkyl or trialkyl phosphites using indium in dilute aqueous HCl at room temperature...
Coordination chemistry of [HFe(CN)(2)(CO)(3)](-) and its derivatives: toward a model for the iron subsite of the [NiFe]-hydrogenasesC Matthew Whaley
Department of Chemistry, University of Illinois at Urbana Champaign, Urbana, Illinois 61801, USA
Inorg Chem 48:4462-9. 2009..Treatment of [K(18-crown-6)][Fe(CN)(2)(CO)(3)] with tertiary phosphines and phosphites gives isomeric mixtures of [HFe(CN)(2)(CO)(2)L](-) (L = P(OPh)(3) and PPh(3))...
Zirconium(IV) compounds as efficient catalysts for synthesis of alpha-aminophosphonatesSrikant Bhagat
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Sector 67, S A S Nagar 160 062, Punjab, India
J Org Chem 73:6029-32. 2008..The reactions were faster with dialkyl/diaryl phosphites than with trialkyl/triaryl phosphites. No O-Me cleavage occurs with aryl methyl ether and methyl ester groups...
Allergic contact dermatitis due to a PVC table coverJ C Salles
Department of Occupational Health, Faculté de Médecine de Reims, 51 rue Cognacq Jay, 51100 Reims, France
Occup Med (Lond) 60:662-4. 2010..Plastics are a common cause of occupational skin disorders such as irritant or allergic contact dermatitis (ACD)...
Site-specific functionalisation of proteins by a Staudinger-type reaction using unsymmetrical phosphitesVerena Böhrsch
Institut fur Chemie und Biochemie, Freie Universitat Berlin, Takustr 3, 14195 Berlin, Germany
Chem Commun (Camb) 46:3176-8. 2010Unsymmetrical phosphites react efficiently in a Staudinger reaction with p-azido-phenylalanine, which can be applied for the biotinylation of proteins, thereby expanding the scope of the chemoselective Staudinger-phosphite reaction of ..
Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] PathwaysIsaac Alonso
Departamento de Quimica Organica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain, Departament de Quimica, Universitat Autonoma de Barcelona, 08193 Bellaterra, Barcelona, Spain, and Instituto de Quimica Organica General CSIC, Juan de la Cierva, 28006, Madrid, Spain
J Am Chem Soc 131:13020-30. 2009Gold(I) complexes featuring electron acceptor ligands such as phosphites and phosphoramidites catalyze the [4C+2C] intramolecular cycloaddition of allenedienes...
Copper-mediated cross-coupling of 1,1-dibromo-1-alkenes with dialkyl phosphites: a convenient synthesis of 1-alkenylphosphonatesGwilherm Evano
Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
Chem Commun (Camb) 47:179-81. 2011..of E-1-alkenylphosphonates by copper-mediated cross-coupling between 1,1-dibromo-1-alkenes and dialkyl phosphites is reported...
Synthesis of novel organic-inorganic hybrid compounds: lanthanide phosphites incorporating a squarate ligandChih Min Wang
Department of Chemistry, National Central University, Jhongli, Taiwan 320, Republic of China
Inorg Chem 48:6335-7. 2009..The photoluminescence properties of the Eu compound have also been studied...
Ligand-promoted carbene insertion into the aryl substituent of an N-heterocyclic carbene ligand in ruthenium-based metathesis catalystsBrandon R Galan
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260 3000
J Am Chem Soc 131:6822-32. 2009..the phosphine-free Hoveyda-Blechert complex Ru(H(2)IMes)(CH(i-PrOC(6)H(4)))Cl(2) by aryl isocyanides and small phosphites but only after initial displacement of the coordinated ether...
Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroboratesMounir Andaloussi
Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry, Uppsala University, BMC, Box 574, 751 23 Uppsala, Sweden
Chemistry 15:13069-74. 2009..Aryl phosphites were also synthesized at room temperature with atmospheric air as the sole reoxidant...
Probing the cytochrome P450-like reactivity of high-valent oxo iron intermediates in the gas phaseM Elisa Crestoni
Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Universita di Roma La Sapienza, P le A Moro 5, I 00185 Roma, Italy
Inorg Chem 44:5379-87. 2005..Whereas CO and cyclohexane proved to be unreactive, olefins, sulfides, amines, and phosphites all undergo oxygen atom transfer in the gas phase yielding the reduction product 1 and/or an adduct ion ([1-S](+)..
A synthesis of phosphorylated dioxohexahydropyrimidines from N,N'-dimethylurea, activated acetylenes, and trialkyl phosphitesIssa Yavari
Chemistry Department, Tarbiat Modares University, P O Box 14115 175, Tehran, Iran
Mol Divers 14:617-20. 2010..This involves the reaction of N,N'-dimethylurea and dialkyl acetylendicarboxylates in the presence of trialkyl phosphites. Under similar conditions, triphenyl phosphite led to alkyl 5-(diphenoxyphosphoryl)-1,3-dimethyl-2,6-dioxo-..
A highly efficient bismuth salts-catalyzed route for the synthesis of α-aminophosphonatesAntara Banik
Department of Chemistry, The University of Texas Pan American, 1201 West University Drive, Edinburg, TX 78541, USA
Molecules 15:8205-13. 2010..types of α-amino phosphonates via one-pot solvent-free three component reactions of aldehydes, amines and phosphites catalyzed by bismuth salts has been investigated...
Asymmetric synthesis of alpha-aminophosphonates using the inexpensive chiral catalyst 1,1'-binaphthol phosphateWeiming Xu
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China
Molecules 15:5782-96. 2010Asymmetric addition under mild conditions of dialkyl phosphites on aldimines derived from cinnamaldehyde catalyzed by the inexpensive chiral organocatalyst (R)-3,3'-[4-fluorophenyl](2)-1,1'-binaphthol phosphate has been found effective to ..
Sulfinimine-mediated asymmetric synthesis of beta-hydroxy alpha-amino phosphonatesFranklin A Davis
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA
J Org Chem 68:7249-53. 2003The addition of potassium dialkyl phosphites to enantiopure O-protected alpha-hydroxy sulfinimine pseudoenantiomers affords beta-hydroxy alpha-amino phosphonates in good yield and de. The reaction exhibits a strong match-mismatch effect.
Transition metal-catalyzed addition reactions of arylboronic acids with alkyl 2-formylbenzoates: efficient access to chiral 3-substituted phthalidesChun Hui Xing
Department of Chemistry, College of Staten Island and the Graduate Center of the City University of New York, 2800 Victory Boulevard, Staten Island, New York 10314, USA
Chem Commun (Camb) 46:3010-2. 2010Transition metal-catalyzed addition of arylboronic acids to 2-formylbenzoates afforded 3-substituted phthalides. By using SPINOL-based phosphites as ligands, a Rh(I)-catalyzed asymmetric version of such an addition reaction was achieved.
DFT study on bifunctional chiral Brønsted acid-catalyzed asymmetric hydrophosphonylation of iminesMasahiro Yamanaka
Department of Chemistry, Faculty of Science, Rikkyo University, 3 34 1 Nishi Ikebukuro, Toshima ku, Tokyo 171 8501 Japan
J Org Chem 74:3266-71. 2009Asymmetric hydrophosphonylation reaction of aldimines with dialkyl phosphites proceeds catalytically by means of a phosphoric acid diester, derived from (R)-BINOL, as a chiral Brønsted acid to afford alpha-amino phosphonates with good to ..
Helical polymers based on intramolecularly hydrogen-bonded aromatic polyamidesYi Xuan Lu
Department of Chemistry, 1102 Natural Sciences 2, University of California, Irvine, CA 92697 2025, USA
Chem Commun (Camb) 46:9019-21. 2010..These polymers can fold into helical conformation different from their linear control. The chirality of helical conformation can further be tuned via acid-base complexation using chiral residues...
Aerobic photooxidation of phosphite esters using diorganotelluride catalystsMakoto Oba
Department of Materials Chemistry, Tokai University, 317 Nishino, Numazu, Shizuoka 410 0395, Japan
Org Lett 11:1879-81. 2009..A Hammett plot with substituted triaryl phosphites yielding rho = 2.88 agrees with a nucleophilic oxygen transfer from telluroxide to phosphite.
An enzymatic fluorescent assay for the quantification of phosphite in a microtiter plate formatOliver Berkowitz
Centre for Phytophthora Science and Management, School of Biological Sciences and Biotechnology, Murdoch University, Murdoch, WA 6150, Australia
Anal Biochem 412:74-8. 2011..Because phosphite is a widely used fungicide to protect plants from pathogenic oomycetes, the assay provides a cost-effective and easy-to-use method to monitor the fate of phosphite following application...
Nitrogen atom transfer from iron(IV) nitrido complexes: a dual-nature transition state for atom transferJeremiah J Scepaniak
Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces New Mexico 88003, United States
Inorg Chem 50:9508-17. 2011..of nitrogen atom transfer from four-coordinate tris(carbene)borate iron(IV) nitrido complexes to phosphines and phosphites has been investigated...
Dinucleotides containing 3'-S-phosphorothiolate linkagesJames W Gaynor
Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK
Methods Mol Biol 764:17-30. 2011..a thymidine dinucleotide and is based on the use of a silyl phosphite, which is more reactive than simple alkyl phosphites and also simplifies the deprotection strategy...
Direct conversion of benzylic and allylic alcohols to phosphonatesRocky J Barney
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242 1294, United States
J Org Chem 76:2875-9. 2011..To identify a more direct synthesis of phosphonate esters, we have developed a one-flask procedure for conversion of benzylic and allylic alcohols to the corresponding phosphonates through treatment with triethyl phosphite and ZnI(2)...
Copper/DIPEA-catalyzed, aldehyde-induced tandem decarboxylation-coupling of natural α-amino acids and phosphites or secondary phosphine oxidesDongxu Yang
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Medicine, and Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, P R China
J Org Chem 76:6426-31. 2011..aldehyde-induced intermolecular decarboxylative coupling reaction of natural α-amino acids and phosphites or secondary phosphine oxides was developed...
Thioether-phosphite: new ligands for the highly enantioselective Ir-catalyzed hydrogenation of minimally functionalized olefinsMercedes Coll
Departament de Quimica Fisica i Inorganica, Universitat Rovira i Virgili, Campus Sescelades, C Marcellí Domingo, s n 43007 Tarragona, Spain
Chem Commun (Camb) 47:9215-7. 2011..Excellent enantioselectivities (ee's up to 99%) have been obtained for a range of substrates, including challenging terminal disubstituted substrates, under standard conditions...
Application of phosphine-phosphite ligands in the iridium catalyzed enantioselective hydrogenation of 2-methylquinolineMiguel Rubio
Instituto de Investigaciones Quimicas, Consejo Superior de Investigaciones Cientificas and Universidad de Sevilla, Avda Americo Vespucio 49, 41092 Sevilla, Spain
Molecules 15:7732-41. 2010The hydrogenation of 2-methylquinoline with Ir catalysts based on chiral phosphine-phosphites has been investigated. It has been observed that the reaction is very sensitive to the nature of the ligand...
Horner-Wadsworth-Emmons reagents as azomethine ylide analogues: pyrrole synthesis via (3 + 2) cycloadditionMarie S T Morin
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada
Org Lett 12:4916-9. 2010..compounds are assembled in one pot via the TMSOTf-catalyzed Arbuzov reaction of imines, acid chlorides, and phosphites. The coupling of this synthesis with alkyne cycloaddition provides a three-component synthesis of pyrroles...
One-step synthesis and bioassay of N-phosphoramidophosphonatesMudumala Veera Narayana Reddy
Department of Chemistry, Sri Venkateswara University, Tirupati, India
Chem Pharm Bull (Tokyo) 57:1391-5. 2009..by a direct reaction of phosphoramidate (1) with heterocyclic aldehydes (2a-j) and dialkyl phosphites at 60-70 degrees C in the presence of tetramethylguanidine...
Simple and catalyst-free synthesis of oxoindolin-3-yl phosphonatesGhazaleh Imani Shakibaei
Department of Chemistry, Shahid Beheshti University, G C, P O Box 19396 4716, Tehran, Iran
J Comb Chem 12:295-7. 2010..of dialkyl or diaryl 3-(dicyanomethyl)-2-oxoindolin-3-ylphosphonates by the reaction of dialkyl or diaryl phosphites and oxoindolin-3-ylidenemalononitriles under solvent-free conditions is reported...
Synthesis and characterization of anti-bisFe(III) porphyrins, syn-bisFe(III)-mu-oxo porphyrin, and syn-bisFe(III)-mu-oxo porphyrin cation radicalSudip Kumar Ghosh
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India
Inorg Chem 49:3449-60. 2010..The complex catalyzes the rapid photoinduced oxygenation of phosphites under mild condition using aerial O(2)...
Highly enantioselective conjugate additions of phosphites to alpha,beta-unsaturated N-acylpyrroles and imines: a practical approach to enantiomerically enriched amino phosphonatesDepeng Zhao
State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology School of Life Sciences, Lanzhou University, Lanzhou 730000, China
Chemistry 15:10983-7. 2009..and enantioselectivities (up to >99 % enantiomeric excess (ee)) were observed for a broad spectrum of both phosphites and N-acylpyrroles under mild conditions...
Aqueous chemistry of chlorocyclophosphazenes: phosphates {PO(2)}, phosphamides {P(O)NHR}, and the first phosphites {PHO} and pyrophosphates {(PO)(2)O} of these heterocyclesJoanne Ledger
Department of Chemistry, University of Liverpool, Crown Street, Liverpool L69 7ZD, United Kingdom
Inorg Chem 49:3896-904. 2010..b>Phosphites E containing PHO moieties are obtained via reduction of the dichloride with potassium and subsequent treatment ..
[Zn(HPO(3))(C(11)N(2)O(2)H(12))] and [Zn(3)(H(2)O)(PO(4))(HPO(4))(C(6)H(9)N(3)O(2))(2) (C(6)H(8)N(3)O(2))]: homochiral zinc phosphite/phosphate networks with biofunctional amino acidsZhaojun Dong
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun, 130012, PR China
Dalton Trans 39:5439-45. 2010..The formation of such chiral one-dimensional structures with multi-amino acids might be potentially applied in chiral catalysis, biochemistry processes or as functional materials...
1-(Alpha-aminobenzyl)-2-naphthol: a new chiral auxiliary for the synthesis of enantiopure alpha-aminophosphonic acidsKirill E Metlushka
Kazan Scientific Center of the Russian Academy of Sciences, A E Arbuzov Institute of Organic and Physical Chemistry, Arbuzov str 8, Kazan 420088, Russia
Chemistry 15:6718-22. 2009..has been developed, based on the reaction, in the presence of trifluoroacetic acid, of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(alpha-aminobenzyl)-2-naphthol...
Phosphoramidate-peptide synthesis by solution- and solid-phase Staudinger-phosphite reactionsRemigiusz A Serwa
Institut fur Chemie und Biochemie, Freie Universitat Berlin, Berlin, Germany
J Pept Sci 16:563-7. 2010..The corresponding Staudinger reactions proceed in high conversion rates and deliver phosphoramidate peptides, in which the modification site is located in the middle of the peptide sequence...
Remarkable levels of enantioswitching in catalytic asymmetric hydroborationSean M Smith
Department of Chemistry, University of Nebraska Lincoln, Lincoln, Nebraska 68588, USA
Org Lett 12:4612-5. 2010TADDOL-derived phosphites and phosphoramidites are effective ligands for rhodium-catalyzed asymmetric hydroborations of β,γ-unsaturated amides, achieving up to 99% ee...
Defining the phosphite-regulated transcriptome of the plant pathogen Phytophthora cinnamomiMichaela King
Centre for Phytophthora Science and Management, School of Biological Sciences and Biotechnology, Murdoch University, Perth, WA 6150, Australia
Mol Genet Genomics 284:425-35. 2010..The results of both the microscopic and molecular investigations are consistent with phosphite inhibiting the function of the cytoskeleton and cell wall synthesis...
Transformation of a layered zinc phosphite to a three-dimensional open-framework structure with intersecting 16- and 12-ring channelsZhien Lin
Fachbereich Chemie, Philipps Universitat Marburg, Hans Meerwein Strasse, D 35043 Marburg, Germany
Inorg Chem 48:3517-9. 2009..The compound could be transformed into a new three-dimensional open-framework zinc phosphite, Zn(2)(H(2)O)(4)(HPO(3))(2) x H(2)O, with intersecting 16- and 12-ring channels at room temperature...
Handling within run retention time shifts in two-dimensional chromatography data using shift correction and modelingThomas Skov
Quality and Technology, Department of Food Science, Faculty of Life Sciences, University of Copenhagen, Rolighedsvej 30, DK 1958 Frederiksberg C, Denmark
J Chromatogr A 1216:4020-9. 2009..The pros and cons of the presented approaches are discussed in relation to the model parameters, the signal-to-noise ratio and the degree of shift...
A new concept for DNA-arraysKerstin Jahn-Hofmann
, , Frankfurt am Main, Germany
Nucleosides Nucleotides Nucleic Acids 22:1479-82. 2003..the four 5'-S-(4,4'-dimethoxytrityl)-mercapto-2'-deoxynucleotide-3'-O-(2-cyanoethoxydiisopropylamino)-phosphites (5a-d). The cleavage of P-S and C-S bonds is described (Mag, M.; Lücking, S.; Engels, J.W...
Triphenyl phosphite neurotoxicity in the hen: inhibition of neurotoxic esterase and of prophylaxis by phenylmethylsulfonyl fluorideC D Carrington
Department of Pharmacology, Duke University Medical Center, Durham, North Carolina 27710
Arch Toxicol 62:375-80. 1988..This high level of NTE inhibition persisted for several weeks. This prolonged inhibition probably accounts for the inability of PMSF to block the neurotoxicity of TOCP.(ABSTRACT TRUNCATED AT 250 WORDS)..
Phosphite accelerates programmed cell death in phosphate-starved oilseed rape (Brassica napus) suspension cell culturesVinay K Singh
Department of Biology, Queen's University, Kingston, Ontario, K7L 3N6, Canada
Planta 218:233-9. 2003..Our results also infer that the adaptive value of acclimating at the molecular level to Pi-stress is to extend the viability of -Pi B. napus cell cultures by about 3 weeks...
Research Grants
- Colorimetric Breathalyzer for Dialysis MonitoringWILLIAM MCNAMARA; Fiscal Year: 2002..has shown that this technology can detect and quantify vapors (including alcohols, amines, ethers, phosphines, phosphites, thioethers and thiols) at the sub-ppm (parts per million) level...
- MICROBIAL METABOLISMS OF REDUCED PHOSPHOROUS COMPOUNDSWILLIAM METCALF; Fiscal Year: 2004..abstract_text> ..
- Syntheses of Amino Acids and Amino Phosphonic AcidsFRANKLIN DAVIS; Fiscal Year: 2005..Targets include cyclic, unsaturated, and, beta substituted derivatives (beta amino, beta hydroxy, and beta fluoro). ..
- ASYMMETRIC SYNTHESIS OF BIOACTIVE PRIMARY AMINESFRANKLIN DAVIS; Fiscal Year: 2006....
- MICROBIAL METABOLISM OF REDUCED PHOSPHORUS COMPOUNDSWILLIAM METCALF; Fiscal Year: 2007....
- Discovery, Design, and Development of Phosphonic Acid AntibioticsWILLIAM METCALF; Fiscal Year: 2007..The project will be housed in the new Institute for Genomic Biology at the University of Illinois, where the program project team will occupy a single, large contiguous laboratory. ..
- Asymmetric Synthesis of Amino Acids and Amino Phosphonic AcidsFRANKLIN DAVIS; Fiscal Year: 2007..The photodesulfmylation of sulfinamides represents an important new protocol, not requiring acids or bases, for the removal of the valuable amine N-sulfinyl protecting group. ..
- EFFICIENT SYNTHESIS OF ENANTIOPURE ALPHA AMINO ACIDSFRANKLIN DAVIS; Fiscal Year: 2001....
- ASYMMETRIC SYNTHESIS OF BIOACTIVE PRIMARY AMINESFRANKLIN DAVIS; Fiscal Year: 2002..New and improved enantioselective approaches to these bioactive amines are expected to result. ..
- Bisphenol A and Phthalate Exposure in Relation to Fetal Growth and Preterm BirthJohn D Meeker; Fiscal Year: 2010....
