Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates

被引：24

作者：

Bull, Steven D.

Davies, Stephen G.

Epstein, Simon W.

Garner, A. Christopher

Mujtaba, Nadeam

Roberts, Paul M.

Savory, Edward D.

Smith, Andrew D.

Tamayo, Juan A.

Watkin, David J.

机构：

[1] Univ Oxford, Dept Organ Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Univ Oxford, Dept Chem Crystallog, Chem Res Lab, Oxford OX1 3TA, England

来源：

TETRAHEDRON | 2006年 / 62卷 / 33期

基金：

英国工程与自然科学研究理事会;

关键词：

enantiodiscrimination; diketopiperazine; 3-methyl-aspartate;

D O I：

10.1016/j.tet.2006.05.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enolates of (S)-N,N'-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione exhibit high levels of enantiodiscrimination in alkylations with (RS)-1-aryl-1-bromoethanes and (RS)-2-bromoesters, affording substituted diketopiperazines containing two new stereogenic centres in high de. Deprotection and hydrolysis of the resultant substituted diketopiperazines provides a route to the asymmetric synthesis of homochiral methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates in high de and ee. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：7911 / 7925

页数：15

共 57 条

[1] Synthesis and analysis of the sterically constrained L-glutamine analogues (3S,4R)-3,4-dimethyl-L-glutamine and (3S,4R)-3,4-dimethyl-L-pyroglutamic acid [J].