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N-对甲苯磺酰基亚胺与甲基乙烯基酮、丙烯醛、丙烯酸苯酯或丙烯酸α-萘酯的高效氮杂-Baylis-Hillman反应:路易斯碱效应及合成α,β-不饱和β-氨基羰基化合物的简便方法

Highly efficient aza-Baylis-Hillman reaction of N-tosylated imines with MVK, acrolein, and phenyl acrylate or alpha-naphthyl acrylate: Lewis base effects and a convenient method to synthesize alpha,beta-unsaturated beta-amino carbonyl compounds.

作者信息

Xu Yong-Mei, Shi Min

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

出版信息

J Org Chem. 2004 Jan 23;69(2):417-25. doi: 10.1021/jo035103p.

DOI:10.1021/jo035103p
PMID:14725455
Abstract

This paper describes several highly efficient aza-Baylis-Hillman reactions of N-tosylated imines with MVK, acrolein, and phenyl acrylate or alpha-naphthyl acrylate in the presence of a Lewis base. In most cases, the reaction can be completed within 1 h using the appropriate Lewis base catalyst. An efficient method to synthesize beta-amino ketones, aldehydes and esters in high yields and short reaction time has been developed.

摘要

本文描述了在路易斯碱存在下,N-对甲苯磺酰亚胺与甲基乙烯基酮、丙烯醛、苯基丙烯酸酯或α-萘基丙烯酸酯发生的几种高效氮杂-Baylis-Hillman反应。在大多数情况下,使用合适的路易斯碱催化剂,反应可在1小时内完成。已开发出一种在短反应时间内高产率合成β-氨基酮、醛和酯的有效方法。

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