Stereoselective reductive amination of β-keto esters derived from dipeptides.: Stereochemical and mechanistic studies on the formation of 5-carboxymethyl-2-oxopiperazine derivatives

被引：11

作者：

Patiño-Molina, R ^{[1
]}

Herranz, R ^{[1
]}

García-López, T ^{[1
]}

González-Muñiz, R ^{[1
]}

机构：

[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 52期

关键词：

peptide mimetics; piperazinones; beta-keto esters;

D O I：

10.1016/S0040-4020(99)00957-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective generation of 3,5-disubstituted and 3,5,6-trisubstituted 2-oxopiperazine derivatives can be accomplished by intramolecular reductive amination of beta-keto esters derived from 2-Xaa-Gly-OH and Z-Xaa-Yaa-OH dipeptides, respectively. Differences in the stereoselectivity between the use df NaBH3CN and hydrogen as reducing agents are due to the reduction of different intermediates, as deduced from experiments of isotopic labelling with deuterium. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：15001 / 15010

页数：10

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