Practical preparation of enantiopure 2-methyl-azetidine-2-carboxylic acid; a γ-turn promoter

被引：24
|
作者：
Drouillat, Bruno [1 ]
Wright, Karen [1 ]
Marrot, Jerome [1 ]
Couty, Francois [1 ]
机构：
[1] Univ Versailles St Quentin Yvelines, Inst Lavoisier de Versailles, CNRS, UMR 8180, F-78035 Versailles, France
来源：
TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 09期
关键词：
AMINO-ACIDS; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; PROLINE; BETA; CONFORMATION; DERIVATIVES;
D O I：
10.1016/j.tetasy.2012.05.006
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A robust and practical synthesis of each enantiomer of 2-methyl-azetidine-2-carboxylic acid, based on the use of (S)-phenylglycinol as resolving agent, is described. This synthesis affords practical quantities of this quaternary amino acid suitably N- and C-protected for use in further peptide coupling. Synthetic highlights include the formation of the azetidine ring by intramolecular alkylation and the facile separation of the diastereoisomeric amides derived from phenylglycinol. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：690 / 696
页数：7
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