Cesium effect: High chemoselectivity in direct N-alkylation of amines

被引：238

作者：

Salvatore, RN ^{[1
]}

Nagle, AS ^{[1
]}

Jung, KW ^{[1
]}

机构：

[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 03期

关键词：

D O I：

10.1021/jo010643c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for the mono-N-alkylation of primary amines, diamines, and polyamines was developed using cesium bases in order to prepare secondary amines efficiently. A cesium base not only promoted alkylation of primary amines but also suppressed overalkylations of the produced secondary amines. Various amines, alkyl bromides, and alkyl sulfonates were examined, and the results demonstrated this methodology was highly chemoselective to favor mono-N-alkylation over dialkylation. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the secondary amines exclusively, offering wide applications in peptidomimetic syntheses.

引用

页码：674 / 683

页数：10

共 48 条

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