Practical Methods for the Synthesis of Symmetrically α,α-Disubstituted α-Amino Acids

被引：128

作者：

Soloshonok, Vadim A. ^{[1
]}

Sorochinsky, Alexander E. ^{[2
]}

机构：

[1] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA

[2] Natl Acad Sci Ukraine, Inst Bioorgan Chem & Petrochem, UA-9402660 Kiev, Ukraine

来源：

SYNTHESIS-STUTTGART | 2010年 / 14期

关键词：

sterically constrained; alpha; alpha-disubstituted alpha-amino acids; dialkylation; nucleophilic glycine equivalents; nickel(II) complexes; MICHAEL ADDITION-REACTIONS; NUCLEOPHILIC GLYCINE EQUIVALENTS; EFFICIENT ASYMMETRIC-SYNTHESIS; VIRTUALLY COMPLETE CONTROL; INDUCED AXIAL CHIRALITY; SUBSTITUTED PYROGLUTAMIC ACIDS; ACHIRAL-PHASE CHROMATOGRAPHY; PURE 4-AMINOGLUTAMIC ACIDS; LARGE-SCALE SYNTHESIS; ONE-POT SYNTHESIS;

D O I：

10.1055/s-0029-1220013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This report provides an overview of the practical methods for preparing symmetrically alpha,alpha-disubstituted alpha-amino acids and their derivatives. Despite the growing application of this particular type of sterically constrained alpha-amino acid in the de novo design of peptides and peptidomimetics, synthetically important achievements in the field have not been summarized so far. Classical methods, such as the Bucherer-Bergs and Strecker reactions of sym-dialkyl and cyclic ketones, as well as recent methods involving dialkylation of nucleophilic glycine equivalents and Ugi reactions, are presented.

引用

页码：2319 / 2344

页数：26

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