Efficient CS2CO3-promoted solution and solid phase synthesis of carbonates and carbamates in the presence of TBAI

被引：81

作者：

Salvatore, RN ^{[1
]}

Chu, FX ^{[1
]}

Nagle, AS ^{[1
]}

Kapxhiu, EA ^{[1
]}

Cross, RM ^{[1
]}

Jung, KW ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2002年 / 58卷 / 17期

基金：

美国国家卫生研究院;

关键词：

carbonates; carbamates; cesium; carbonate;

D O I：

10.1016/S0040-4020(02)00286-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel solution and solid-phase methods for the synthesis of carbonates and carbamates were developed using cesium bases and TBAT via a three-component coupling. Cesium carbonate not only promoted successful carbonylations of alcohols and carbamations of amines, but also suppressed common side reactions traditionally seen using existing protocols. Various alcohols and amines were examined, using a wide array of alkyl halides. and the results demonstrated this methodology was highly chemoselective. In particular, use of either sterically demanding substrates or amino acid derivatives afforded the corresponding products exclusively, offering a wide variety of applications such as novel protecting groups and peptidomimetic syntheses. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3329 / 3347

页数：19

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