NOVEL MODIFICATIONS OF PEPTIDES - SIMPLE SYNTHESES OF DIFUNCTIONALIZED ENAMINES, ENOL ETHERS, AND THIOENOL ETHERS FROM CARBOXYLIC-ACIDS VIA ACYLIMIDAZOLE AND ENOL PHOSPHATE INTERMEDIATES

被引：20

作者：

SAUVE, G

LEBERRE, N

ZACHARIE, B

机构：

[1] Institut Armand-Frappier Universite du Quebec, Laval Quebec, Canada H7N 4Z3

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 10期

关键词：

D O I：

10.1021/jo00297a008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The condensation of carboxylic acids 5 (N-protected amino acids or dipeptides) and active methylene compounds to give difunctionalized enols 6 is accomplished by the use of 1,1’-carbonyldiimidazole as an activating reagent. Enamines 7a, enol ethers 7b, and thioenol ethers 7c are obtained directly from the corresponding nucleophiles and the intermediates formed from enols 6 by the action of phenyl phosphorodichloridate. The integrity of peptide chiral centers is maintained during these transformations. © 1990, American Chemical Society. All rights reserved.

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页码：3002 / 3004

页数：3

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