José R Pedro

Summary

Affiliation: University of Valencia
Country: Spain

Publications

  1. doi request reprint Enantioselective alkynylation of benzo[e][1,2,3]-oxathiazine 2,2-dioxides catalysed by (R)-VAPOL-Zn complexes: synthesis of chiral propargylic cyclic sulfamidates
    Lode De Munck
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner 50, 46100 Burjassot, Valencia, Spain
    Org Biomol Chem 13:7393-6. 2015
  2. doi request reprint Highly enantioselective aza-Henry reaction with isatin N-Boc ketimines
    Melireth Holmquist
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner 50, E 46100 Burjassot Valencia, Spain
    Chem Commun (Camb) 50:9309-12. 2014
  3. doi request reprint Catalytic asymmetric conjugate addition of terminal alkynes to β-trifluoromethyl α,β-enones
    Amparo Sanz-Marco
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner 50, 46100 Burjassot, Spain
    Chem Commun (Camb) 50:2275-8. 2014
  4. doi request reprint NMR spectroscopic characterization and DFT calculations of zirconium(IV)-3,3'-Br2-BINOLate and related complexes used in an enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated ketones
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner 50, E 46100 Burjassot, Valencia, Spain
    J Org Chem 77:10545-56. 2012
  5. doi request reprint Synthesis of functionalized indoles with a trifluoromethyl-substituted stereogenic tertiary carbon atom through an enantioselective Friedel-Crafts alkylation with beta-trifluoromethyl-alpha,beta-enones
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner 59, 46100 Burjassot, Valencia, Spain
    Chemistry 16:9117-22. 2010
  6. ncbi request reprint Catalytic asymmetric addition of dimethylzinc to alpha-ketoesters, using mandelamides as ligands
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner, 50, E 46100 Burjassot, Spain
    Org Lett 8:1287-90. 2006
  7. doi request reprint Highly enantioselective nitrone cycloadditions with 2-alkenoyl pyridine N-oxides catalyzed by Cu(II)-BOX complexes
    Santiago Barroso
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner, 50, E 46100 Burjassot, Valencia, Spain
    Org Lett 13:402-5. 2011
  8. doi request reprint Enantioselective zinc/BINOL-catalysed alkynylation of aldimines generated in situ from α-amido sulfones
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner 50, 46100 Burjassot, Spain
    Chemistry 18:2440-4. 2012
  9. ncbi request reprint Syntheses of (+)-alismoxide and (+)-4-epi-alismoxide
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner 50, E 46100, Burjassot, Valencia, Spain
    J Org Chem 71:7866-9. 2006
  10. doi request reprint Enantioselective Henry addition of methyl 4-nitrobutyrate to aldehydes. Chiral building blocks for 2-pyrrolidinones and other derivatives
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner, 50, E 46100 Burjassot Valencia, Spain
    Org Lett 12:3058-61. 2010

Collaborators

  • Gonzalo Blay
  • Luis R Domingo
  • M Carmen Muñoz
  • Amparo Sanz-Marco
  • Melireth Holmquist
  • Santiago Barroso
  • Alicia Monleón
  • Lode De Munck
  • Andrea García-Ortiz
  • Miguel Espinosa
  • Carlos Vila
  • Isabel Fernandez
  • Luz Cardona
  • Lina Al-Midfa

Detail Information

Publications24

  1. doi request reprint Enantioselective alkynylation of benzo[e][1,2,3]-oxathiazine 2,2-dioxides catalysed by (R)-VAPOL-Zn complexes: synthesis of chiral propargylic cyclic sulfamidates
    Lode De Munck
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner 50, 46100 Burjassot, Valencia, Spain
    Org Biomol Chem 13:7393-6. 2015
    ....
  2. doi request reprint Highly enantioselective aza-Henry reaction with isatin N-Boc ketimines
    Melireth Holmquist
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner 50, E 46100 Burjassot Valencia, Spain
    Chem Commun (Camb) 50:9309-12. 2014
    ..The reaction, which does not require protection of the N1 atom, provides the corresponding nitroamines bearing a quaternary stereocentre with high yields and enantiomeric excesses (up to 99.9%)...
  3. doi request reprint Catalytic asymmetric conjugate addition of terminal alkynes to β-trifluoromethyl α,β-enones
    Amparo Sanz-Marco
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner 50, 46100 Burjassot, Spain
    Chem Commun (Camb) 50:2275-8. 2014
    ..Ketones bearing a trifluoromethylated propargylic chiral centre in the β-position were obtained with good yields and high enantiomeric excesses (up to 99%). ..
  4. doi request reprint NMR spectroscopic characterization and DFT calculations of zirconium(IV)-3,3'-Br2-BINOLate and related complexes used in an enantioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated ketones
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner 50, E 46100 Burjassot, Valencia, Spain
    J Org Chem 77:10545-56. 2012
    ..Finally a plausible mechanism for the Friedel-Crafts reaction and a stereomodel for the mode of action of the catalyst that explain the observed stereochemistry of the reaction products have been proposed...
  5. doi request reprint Synthesis of functionalized indoles with a trifluoromethyl-substituted stereogenic tertiary carbon atom through an enantioselective Friedel-Crafts alkylation with beta-trifluoromethyl-alpha,beta-enones
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner 59, 46100 Burjassot, Valencia, Spain
    Chemistry 16:9117-22. 2010
    ..The reaction can be applied to a large number of substituted alpha-trifluoromethyl enones and substituted indoles. The expected products were obtained with good yields and ees of up to 99%...
  6. ncbi request reprint Catalytic asymmetric addition of dimethylzinc to alpha-ketoesters, using mandelamides as ligands
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner, 50, E 46100 Burjassot, Spain
    Org Lett 8:1287-90. 2006
    ..Mandelamides having deprotonated alcohol and carboxyamido groups catalyzed the addition of dimethylzinc to alpha-ketoesters with good yields and ee (up to 90%)...
  7. doi request reprint Highly enantioselective nitrone cycloadditions with 2-alkenoyl pyridine N-oxides catalyzed by Cu(II)-BOX complexes
    Santiago Barroso
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner, 50, E 46100 Burjassot, Valencia, Spain
    Org Lett 13:402-5. 2011
    ..The reaction is catalyzed by Cu(II)-BOX complexes to give the expected isoxazolidine products with high diastereo- and enantioselectivity...
  8. doi request reprint Enantioselective zinc/BINOL-catalysed alkynylation of aldimines generated in situ from α-amido sulfones
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner 50, 46100 Burjassot, Spain
    Chemistry 18:2440-4. 2012
    ..The reactions give good yields and high enantioselectivities (ee values up to 95 %) for a good number of aromatic and heteroaromatic α-amido sulfones and alkynes...
  9. ncbi request reprint Syntheses of (+)-alismoxide and (+)-4-epi-alismoxide
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner 50, E 46100, Burjassot, Valencia, Spain
    J Org Chem 71:7866-9. 2006
    ..6 value indicates that significant amounts of alismoxide result from biosynthetic processes. Furthermore, the structure of the natural guaienediol isolated from Silphium perfoliatum has been corrected to (-)-alismoxide...
  10. doi request reprint Enantioselective Henry addition of methyl 4-nitrobutyrate to aldehydes. Chiral building blocks for 2-pyrrolidinones and other derivatives
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner, 50, E 46100 Burjassot Valencia, Spain
    Org Lett 12:3058-61. 2010
    ..These products have been transformed into nonracemic chiral gamma-lactams, 5-hydroxy-5-substituted levulinic acid derivatives, and delta-lactones...
  11. doi request reprint Enantioselective zirconium-catalyzed Friedel-Crafts alkylation of pyrrole with trifluoromethyl ketones
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner 50, E 46100 Burjassot Valencia, Spain
    Org Lett 11:441-4. 2009
    ..The absolute stereochemistry of the products has been determined by chemical correlation...
  12. ncbi request reprint Total syntheses of four stereoisomers of 4alpha-hydroxy-1beta,7beta-peroxy- 10betaH-guaia-5-ene
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Spain
    Org Lett 7:3291-4. 2005
    ..The structure of the natural 4alpha-hydroxy-1beta,7beta-peroxy-10betaH-guaia-5-ene isolated from Liabum floribundum has been confirmed...
  13. ncbi request reprint Nucleophilic benzoylation using a mandelic acid dioxolanone as a synthetic equivalent of the benzoyl carbanion. Oxidative decarboxylation of alpha-hydroxyacids
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, E 46100 Burjassot Valencia, Spain
    Molecules 9:365-72. 2004
    ..The last step is carried out in a catalytic aerobic way using a Co (III) complex in the presence of pivalaldehyde under very mild conditions...
  14. ncbi request reprint Enantioselective synthesis of tertiary alcohols through a zirconium-catalyzed Friedel-Crafts alkylation of pyrroles with α-ketoesters
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner 50, E 46100 Burjassot Valencia, Spain
    J Org Chem 76:6286-94. 2011
    ..The reaction is also of application to 4,7-dihydroindole to give C2-alkylated indoles after oxidation with p-benzoquinone...
  15. ncbi request reprint Rearrangement of 4,5-epoxy-9-trimethylsilyldecalines. Application to the synthesis of the natural eremophilane (-)-aristolochene
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, 46100 Burjassot Valencia, Spain
    J Org Chem 71:4929-36. 2006
    ..The synthetic utility of these rearrangements is shown by the synthesis of natural (-)-aristolochene...
  16. doi request reprint Highly enantioselective copper(I)-catalyzed conjugate addition of terminal alkynes to 1,1-difluoro-1-(phenylsulfonyl)-3-en-2-ones: new ester/amide surrogates in asymmetric catalysis
    Amparo Sanz-Marco
    Department de Química Orgànica Facultat de Química, Universitat de Valencia, C Dr Moliner 50, 46100 Burjassot Valencia Spain, Fax 34 963544328
    Chemistry 20:668-72. 2014
    ..This is the first example on the use of 1,1-difluoro-1-(phenylsulfonyl)-3-en-2-ones as substrates in an enantioselective reaction, which have been shown to be new ester/amide surrogates. ..
  17. doi request reprint Synthesis of densely functionalised 5-halogen-1,3-oxazin-2-ones by halogen-mediated regioselective cyclisation of N-Cbz-protected propargylic amines: a combined experimental and theoretical study
    Alicia Monleón
    Department de Química Orgànica Facultat de Química, Universitat de Valencia, C Dr Moliner 50, 46100 Burjassot Valencia Spain, Fax 34 963544328
    Chemistry 19:14852-60. 2013
    ..To rationalise the experimental results, theoretical studies at the B3LYP/6-311G* level have been performed...
  18. ncbi request reprint Enantioselective copper-aminopyridine-catalyzed aza-Henry reaction with chelating N-(2-pyridyl)sulfonyl imines
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Burjassot, Spain
    Chirality 24:441-50. 2012
    ..An example of transformation of these compounds into N-(2-pyridyl)sulfonyl-α-amino acids and deprotection of the sulfonamide with Mg-MeOH is provided...
  19. doi request reprint Enantioselective addition of nitromethane to 2-acylpyridine N-oxides. Expanding the generation of quaternary stereocenters with the Henry reaction
    Melireth Holmquist
    Departament de Quimica Organica, Facultat de Química Universitat de València, C Dr Moliner 50, E 46100Burjassot València, Spain
    Org Lett 16:1204-7. 2014
    ....
  20. ncbi request reprint A bioinspired approach to tri-nor-guaianes. synthesis of (-)-clavukerin A
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, Dr Moliner 50, E 46100, Burjassot, Valencia, Spain
    J Nat Prod 69:1234-6. 2006
    ..The starting guaiadienone is readily obtained from commercially available santonin or (+)-dihydrocarvone...
  21. doi request reprint The construction of quaternary stereocenters by the Henry reaction: circumventing the usual reactivity of substituted glyoxals
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner 50, Burjassot Valencia, Spain
    Chemistry 17:3768-73. 2011
    ..Both aromatic and aliphatic glyoxals are suitable substrates for this reaction...
  22. doi request reprint Asymmetric conjugate addition of malonate esters to α,β-unsaturated N-sulfonyl imines: an expeditious route to chiral δ-aminoesters and piperidones
    Miguel Espinosa
    Department de Química Orgànica Facultat de Química, Universitat de Valencia, C Dr Moliner 50, 46100 Burjassot, Valencia Spain, Fax 34 963544328
    Chemistry 19:14861-6. 2013
    ..The reaction gives the corresponding E enamines bearing a stereogenic center at the allylic position with good yields and enantiomeric ratios up to 97:3. This reaction provides a synthetic entry to chiral δ-aminoesters and piperidones. ..
  23. doi request reprint Enantioselective zinc-mediated conjugate addition of terminal alkynes to enones
    Gonzalo Blay
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner 50, E 46100 Burjassot Valencia, Spain
    Chemistry 18:12966-9. 2012
    ..The products can be enantiomerically enriched up to 99% ee by crystallization (see scheme)...
  24. doi request reprint Copper(II)-bis(oxazoline) catalyzed asymmetric Diels-Alder reaction with alpha'-arylsulfonyl enones as dienophiles
    Santiago Barroso
    Departament de Quimica Organica, Facultat de Quimica, Universitat de Valencia, C Dr Moliner, 50, E 46100 Burjassot Valencia, Spain
    J Org Chem 73:6389-92. 2008
    ..The resulting products can be alkylated and the sulfone removed, so alpha'-arylsulfonyl enones can be regarded as surrogates of simple monodentate enones, which are poor dienophiles with this catalytic system...