Recent approaches for asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes

被引：78

作者：

Wang, Yibing ^{[1
,2
]}

Song, Xiaohan ^{[1
,2
]}

Wang, Jiang ^{[1
,2
]}

Moriwaki, Hiroki ^{[3
]}

Soloshonok, Vadim A. ^{[4
,5
]}

Liu, Hong ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China

[2] Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China

[3] Hamari Chem Ltd, Higashi Yodogawa Ku, 1-4-29 Kunijima, Osaka 5330024, Japan

[4] Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, Paseo Manuel Lardizabal 3, San Sebastian 20018, Spain

[5] Basque Fdn Sci, Ikerbasque, Maria Diaz de Haro 3, Bilbao 48013, Spain

来源：

AMINO ACIDS | 2017年 / 49卷 / 09期

基金：

中国国家自然科学基金;

关键词：

Asymmetric synthesis; alpha-Amino acids; Tailor-made amino acids; Ni(II) complexes; Practicality; MICHAEL ADDITION-REACTIONS; NUCLEOPHILIC GLYCINE EQUIVALENTS; CHIRAL NICKEL(II) GLYCINATE; DYNAMIC KINETIC RESOLUTION; SUBSTITUTED GLUTAMIC ACIDS; SCHIFF-BASE; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; GENERAL-METHOD; (1R; 2S)-1-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID;

D O I：

10.1007/s00726-017-2458-6

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

This review article critically discusses examples of asymmetric synthesis of tailor-made alpha-amino acids via homologation of Ni(II) complexes of glycine and alanine Schiff bases, reported in the literature from 2013 through the end of 2016. Where it is possible, reaction mechanism and origin of the stereochemical outcome is discussed in detail. Special attention is given to various aspects of practicality and scalability of the reported methods. Among the most noticeable developments in this area are novel designs of axially chiral ligands, application of electro- and mechano-chemical (ball-milling) conditions, and development of dynamic kinetic resolution procedures.

引用

页码：1487 / 1520

页数：34

共 174 条

[11] Chiral sulfoxide controlled asymmetric additions to C-N double bond.: An efficient approach to stereochemically defined α-fluoroalkyl amino compounds [J].