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Stereoselective Synthesis of anti ‐β‐Hydroxy‐α‐amino Acids through Dynamic Kinetic Resolution
Author(s) -
Makino Kazuishi,
Goto Takayuki,
Hiroki Yasuhiro,
Hamada Yasumasa
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200353072
Subject(s) - diastereomer , kinetic resolution , binap , stereoselectivity , chemistry , catalysis , amino acid , resolution (logic) , asymmetric hydrogenation , organic chemistry , stereochemistry , enantioselective synthesis , combinatorial chemistry , biochemistry , computer science , artificial intelligence
Upping the anti : Asymmetric anti ‐selective hydrogenation of α‐amino‐β‐keto esters through dynamic kinetic resolution has been achieved for the first time by using the Ru–binap catalyst. The reaction affords important anti ‐β‐hydroxy‐α‐amino acids with 74–98 % ee and high diastereomeric ratio in excellent yields (see scheme; binap=2,2′‐bis(diphenylphosphanyl)‐1,1′‐binaphthyl).