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Asymmetric Reductive Amination of α-Keto Acids Using Ir-Based Hydrogen Transfer Catalysts: An Access to Unprotected Unnatural α-Amino Acids.
Yajima, Takaaki; Katayama, Akito; Ito, Tsubasa; Kawada, Takuma; Yabushita, Kenya; Yasuda, Toshihisa; Ohta, Takeshi; Katayama, Takeaki; Utsumi, Noriyuki; Kayaki, Yoshihito; Kuwata, Shigeki.
Afiliación
  • Yajima T; Central Research Laboratory, Technology & Development Division, Kanto Chemical Company, Inc., 7-1, Inari 1-chome, Soka-city, Saitama 340-0003, Japan.
  • Katayama A; Central Research Laboratory, Technology & Development Division, Kanto Chemical Company, Inc., 7-1, Inari 1-chome, Soka-city, Saitama 340-0003, Japan.
  • Ito T; Central Research Laboratory, Technology & Development Division, Kanto Chemical Company, Inc., 7-1, Inari 1-chome, Soka-city, Saitama 340-0003, Japan.
  • Kawada T; Central Research Laboratory, Technology & Development Division, Kanto Chemical Company, Inc., 7-1, Inari 1-chome, Soka-city, Saitama 340-0003, Japan.
  • Yabushita K; Central Research Laboratory, Technology & Development Division, Kanto Chemical Company, Inc., 7-1, Inari 1-chome, Soka-city, Saitama 340-0003, Japan.
  • Yasuda T; Central Research Laboratory, Technology & Development Division, Kanto Chemical Company, Inc., 7-1, Inari 1-chome, Soka-city, Saitama 340-0003, Japan.
  • Ohta T; Central Research Laboratory, Technology & Development Division, Kanto Chemical Company, Inc., 7-1, Inari 1-chome, Soka-city, Saitama 340-0003, Japan.
  • Katayama T; Central Research Laboratory, Technology & Development Division, Kanto Chemical Company, Inc., 7-1, Inari 1-chome, Soka-city, Saitama 340-0003, Japan.
  • Utsumi N; Central Research Laboratory, Technology & Development Division, Kanto Chemical Company, Inc., 7-1, Inari 1-chome, Soka-city, Saitama 340-0003, Japan.
  • Kayaki Y; Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-E4-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan.
  • Kuwata S; Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, 1-1-1 Noji-higashi, Kusatsu, Shiga 525-8577, Japan.
Org Lett ; 26(7): 1426-1431, 2024 Feb 23.
Article en En | MEDLINE | ID: mdl-38334425
ABSTRACT
A direct asymmetric reductive amination of α-keto acids catalyzed by Cp*Ir complexes bearing a chiral N-(2-picolyl)sulfonamidato ligand is described. The combined use of optically active 2-phenyglycinol as an aminating agent is effective for the chemo- and stereoselective transfer hydrogenation using formic acid. The subsequent elimination of the hydroxyethyl moiety by orthoperiodic acid can afford various unprotected α-amino acids in satisfactory isolated yields (20 examples) with excellent optical purities (up to >99% ee).
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos