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Chemical Kinetic Resolution of Unprotected β‐Substituted β‐Amino Acids Using Recyclable Chiral Ligands
Author(s) -
Zhou Shengbin,
Wang Jiang,
Chen Xia,
Aceña José Luis,
Soloshonok Vadim A.,
Liu Hong
Publication year - 2014
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.201403556
Subject(s) - sitagliptin , kinetic resolution , amino acid , aryl , enantioselective synthesis , chemistry , combinatorial chemistry , resolution (logic) , alkyl , organic chemistry , catalysis , biochemistry , computer science , biology , metformin , artificial intelligence , diabetes mellitus , endocrinology
The first chemical method for resolution of N,C‐unprotected β‐amino acids was developed through enantioselective formation and disassembly of nickel(II) complexes under operationally convenient conditions. The specially designed chiral ligands are inexpensive and can be quantitatively recycled along with isolation of the target β‐substituted‐β‐amino acids in good yields and excellent enantioselectivity. The method features a broad synthetic generality including β‐aryl, β‐heteroaryl, and β‐alkyl‐derived β‐amino acids. The procedure is easily scaled up, and was used for the synthetically and economically advanced preparation of the anti‐diabetic drug sitagliptin.