Takayoshi Arai

Summary

Affiliation: Chiba University
Country: Japan

Publications

  1. doi request reprint Catalytic asymmetric Friedel-Crafts/protonation of nitroalkenes and N-heteroaromatics
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    J Org Chem 76:5450-6. 2011
  2. ncbi request reprint A trinuclear Zn3(OAc)4-3,3'-bis(aminoimino)binaphthoxide complex for highly efficient catalytic asymmetric iodolactonization
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, 1 33 Yayoi, Inage Ku, Chiba, Japan
    Chem Commun (Camb) 50:8287-90. 2014
  3. doi request reprint Development of a tailor-made bis(oxazolidine)pyridine-metal catalyst for the [3+2] cycloaddition of azomethine imines with propiolates
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, 1 33 Inage, Chiba 263 8522, Japan
    Chem Commun (Camb) 49:7776-8. 2013
  4. doi request reprint Catalytic asymmetric synthesis of mixed 3,3'-bisindoles and their evaluation as Wnt signaling inhibitors
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, 1 33 Yayoi, Chiba 263 8522, Japan
    Angew Chem Int Ed Engl 52:2486-90. 2013
  5. doi request reprint A Neutral, Chiral, Bis(imidazolidine)-Derived NCN-Type Palladium Pincer Complex with Catalytic Activity
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522 Japan, Fax 81 43 290 2889
    Chemistry 19:1554-7. 2013
  6. ncbi request reprint syn-Selective Asymmetric Mannich Reaction of Sulfonyl Imines with Iminoesters Catalyzed by the N,N,N-Tridentate Bis(imidazolidine)pyridine (PyBidine)-Cu(OTf)(2) Complex
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522 Japan, Fax 81 43 290 2889
    Chemistry 18:11219-22. 2012
  7. doi request reprint Chiral bis(imidazolidine)pyridine-cu complex-catalyzed enantioselective [3+2]-cycloaddition of azomethine imines with propiolates
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, 1 33 Yayoi, Inage, Chiba 263 8522, Japan
    Molecules 17:6170-8. 2012
  8. doi request reprint Asymmetric syn-selective Henry reaction catalyzed by the sulfonyldiamine-CuCl-pyridine system
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    J Org Chem 73:4903-6. 2008
  9. ncbi request reprint Organic-inorganic hybrid polymer-encapsulated magnetic nanobead catalysts
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    Chemistry 14:882-5. 2008
  10. doi request reprint A library of chiral imidazoline-aminophenol ligands: discovery of an efficient reaction sphere
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    Chemistry 14:2052-9. 2008

Collaborators

Detail Information

Publications22

  1. doi request reprint Catalytic asymmetric Friedel-Crafts/protonation of nitroalkenes and N-heteroaromatics
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    J Org Chem 76:5450-6. 2011
    ..The anti-adducts could be successfully transformed to biochemically important α-substituted β-heteroarylalkylamines...
  2. ncbi request reprint A trinuclear Zn3(OAc)4-3,3'-bis(aminoimino)binaphthoxide complex for highly efficient catalytic asymmetric iodolactonization
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, 1 33 Yayoi, Inage Ku, Chiba, Japan
    Chem Commun (Camb) 50:8287-90. 2014
    ..Using the harmony of the tri-zinc atoms, 1 mol% Zn3(OAc)4-3,3'-bis(aminoimino)binaphthoxide catalyzed asymmetric iodolactonization in up to 99.9% ee. ..
  3. doi request reprint Development of a tailor-made bis(oxazolidine)pyridine-metal catalyst for the [3+2] cycloaddition of azomethine imines with propiolates
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, 1 33 Inage, Chiba 263 8522, Japan
    Chem Commun (Camb) 49:7776-8. 2013
    ..The PyBodine(l-Ala)-Cu(OAc)2 catalyst was selected on the basis of solid-phase catalysis/CD-HTS and exhibited high efficiency, producing the (R)-adducts with excellent enantioselectivity. ..
  4. doi request reprint Catalytic asymmetric synthesis of mixed 3,3'-bisindoles and their evaluation as Wnt signaling inhibitors
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, 1 33 Yayoi, Chiba 263 8522, Japan
    Angew Chem Int Ed Engl 52:2486-90. 2013
    ..Biological activity of the newly formed chiral 3,3'-bisindoles was also confirmed in a Wnt signaling inhibitory assay...
  5. doi request reprint A Neutral, Chiral, Bis(imidazolidine)-Derived NCN-Type Palladium Pincer Complex with Catalytic Activity
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522 Japan, Fax 81 43 290 2889
    Chemistry 19:1554-7. 2013
    ..The neutral palladium/chloride version exhibited significant catalytic activity for the reaction of nitroalkenes with malononitrile to give products in a highly enantioselective manner...
  6. ncbi request reprint syn-Selective Asymmetric Mannich Reaction of Sulfonyl Imines with Iminoesters Catalyzed by the N,N,N-Tridentate Bis(imidazolidine)pyridine (PyBidine)-Cu(OTf)(2) Complex
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522 Japan, Fax 81 43 290 2889
    Chemistry 18:11219-22. 2012
    ..For both 4-toluene (Ts)- and 4-nitrophenylsulfonyl (Ns)-imines, the syn-adducts were obtained in up to 99 % ee...
  7. doi request reprint Chiral bis(imidazolidine)pyridine-cu complex-catalyzed enantioselective [3+2]-cycloaddition of azomethine imines with propiolates
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, 1 33 Yayoi, Inage, Chiba 263 8522, Japan
    Molecules 17:6170-8. 2012
    ..3+2] Cycloaddition of azomethine imines with electron-deficient terminal alkynes was smoothly catalyzed by a chiral bis(imidazolidine)pyridine-CuOAc complex to give bicyclic pyrazolo[1,2-a]pyrazolone derivatives with up to 74% ee...
  8. doi request reprint Asymmetric syn-selective Henry reaction catalyzed by the sulfonyldiamine-CuCl-pyridine system
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    J Org Chem 73:4903-6. 2008
    ..Moreover, the 2d-CuCl-pyridine system promotes the diastereoselective Henry reaction in syn-selective manner to give the adduct in up to 99% yield with 92:8 syn/ anti selectivity. The enantiomeric excess of the syn-adduct was 84% ee...
  9. ncbi request reprint Organic-inorganic hybrid polymer-encapsulated magnetic nanobead catalysts
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    Chemistry 14:882-5. 2008
    ....
  10. doi request reprint A library of chiral imidazoline-aminophenol ligands: discovery of an efficient reaction sphere
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    Chemistry 14:2052-9. 2008
    ..The unique reaction sphere of L25 was also examined in a Friedel-Crafts alkylation of indole and nitroalkene to give the adduct in up to 83 % ee...
  11. doi request reprint Tandem catalytic asymmetric Friedel-Crafts/Henry reaction: control of three contiguous acyclic stereocenters
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    Angew Chem Int Ed Engl 47:4989-92. 2008
  12. doi request reprint Easy access to fully functionalized chiral tetrahydro-β-carboline alkaloids
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    J Org Chem 76:2909-12. 2011
    ....
  13. doi request reprint Formation of multi-stereogenic centers using a catalytic diastereoselective Henry reaction
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    Chem Commun (Camb) 46:7936-8. 2010
    ..In the reaction of (S)-2-phenylpropanal and nitroethane, the (R,R,R)-L1-CuCl catalyst yielded the expected three contiguous stereogenic centers in a highly syn-selective Henry reaction...
  14. doi request reprint Chiral bis(imidazolidine)pyridine-Cu(OTf)2: catalytic asymmetric endo-selective [3 + 2] cycloaddition of imino esters with nitroalkenes
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522, Japan
    J Am Chem Soc 132:5338-9. 2010
    ..Use of the PyBidine-Cu(OTf)(2) complex as a catalyst enabled the highly endo-selective reaction of imino esters and nitroalkenes to give the adducts in up to 99% ee...
  15. ncbi request reprint Diversity-oriented asymmetric catalysis (DOAC): stereochemically divergent synthesis of thiochromanes using an imidazoline-aminophenol-nickel-catalyzed Michael/Henry reaction
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, 1 33 Yayoi, Inage, Chiba 263 8522, Japan
    Org Lett 16:1700-3. 2014
    ..Reduction of the nitro group of the chiral thiochromanes gave a new series of (2S,3R,4R)-3-amino-2-arylthiochroman-4-ols with retention of the strereoselectivity. ..
  16. ncbi request reprint Catalytic asymmetric protonation of lithium enolates using amino acid derivatives as chiral proton sources
    Kaori Mitsuhashi
    Graduate School of Science and Technology, Chiba University, Inage, Chiba 263 8522, Japan
    Org Lett 8:1721-4. 2006
    ..The enantiomeric excess (up to 88% ee) of the products obtained in the presence of a catalytic amount of the chiral proton source was higher than those obtained in the stoichiometric reaction...
  17. ncbi request reprint An imidazoline-aminophenol (IAP) nickel catalyst: structure and catalytic activity in the enantioselective 1,4-addition of 3'-indolyl-3-oxindoles to nitroethylene
    Atsuko Awata
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522 Japan, Fax 81 43 290 2889
    Chemistry 20:2470-7. 2014
    ..From the optically active 3,3'-mixed indole adduct, biologically important 3'-indolyl-3-pyrrolidinoindoline was successfully synthesized in a three-step reaction sequence...
  18. ncbi request reprint Enantioselective protonation of silyl enolates catalyzed by a BinapAgF complex
    Akira Yanagisawa
    Department of Chemistry, Faculty of Science, Chiba University, Inage, Chiba 263 8522, Japan
    Angew Chem Int Ed Engl 44:1546-8. 2005
  19. ncbi request reprint A novel indole compound, AWT-489, inhibits prostaglandin D2-induced CD55 expression by acting on DP prostanoid receptors as an antagonist in LS174T human colon cancer cells
    Satomi Oyama
    Laboratory of Chemical Pharmacology, Graduate School of Pharmaceutical Sciences, Chiba University, 1 8 1 Inohana, Chuo Ku, Chiba 260 8675, Japan
    Arch Biochem Biophys 541:21-9. 2014
    ..We believe that AWT-489 has potential as a lead compound for designing a new DP receptor antagonist that may help improve PGD2-related diseases, especially colon cancer in the near future...
  20. ncbi request reprint Bis(imidazolidine)pyridine-NiCl2 Catalyst for nitro-Mannich reaction of isatin-derived N-Boc ketimines: asymmetric synthesis of chiral 3-substituted 3-amino-2-oxindoles
    Takayoshi Arai
    Department of Chemistry, Graduate School of Science, Chiba University, 1 33 Yayoi, Inage, Chiba 263 8522, Japan
    Org Lett 16:2768-71. 2014
    ....
  21. ncbi request reprint Catalytic Asymmetric exo'-Selective [3+2] Cycloaddition for Constructing Stereochemically Diversified Spiro[pyrrolidin-3,3'-oxindole]s
    Atsuko Awata
    Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263 8522 Japan, Fax 81 43 290 2889
    Chemistry 18:8278-82. 2012
    ..By using the imidazoline-aminophenol-ligand complex [Ni(OAc)(2) -(L1)], the reaction proceeds in the stepwise Michael-Mannich reaction to give the exo' adducts as stable isomers...
  22. ncbi request reprint Relationship of stereochemical and skeletal diversity of small molecules to cellular measurement space
    Young Kwon Kim
    Howard Hughes Medical Institute, Department of Chemistry and Chemical Biology, and The Eli and Edythe Broad Institute, Program in Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA
    J Am Chem Soc 126:14740-5. 2004
    ..These studies illustrate a quantitative method for measuring stereochemical and skeletal diversity of small molecules and their cellular consequences...