A copper(II)-catalyzed, sequential Michael-aldol reaction for the preparation of 1,2-dihydroquinolines

被引：15

作者：

Wagner, Anna M.

Knezevic, Claire E.

Wall, Jessica L.

Sun, Victoria L.

Buss, Joshua A.

Allen, LeeAnn T.

Wenzel, Anna G. ^{[1
]}

机构：

[1] Claremont Mckenna Coll, Keck Sci Dept, Claremont, CA 91711 USA

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 07期

基金：

美国国家科学基金会;

关键词：

Heterocycles; Lewis acid catalysis; Michael-aldol reaction; Acetonitrile; Small-molecule synthesis; ALPHA; BETA-UNSATURATED N-ACYLPYRROLES; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; DIELS-ALDER REACTION; CONVENIENT SYNTHESIS; CONJUGATE ADDITION; FACILE SYNTHESIS; DERIVATIVES; ACID; METATHESIS; QUINOLINES;

D O I：

10.1016/j.tetlet.2011.12.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper(II)-catalyzed, sequential Michael addition-aldol condensation reaction of N-carboxybenzyl-protected aminobenzaldehyde with various alpha,beta-unsaturated N-acyl pyrroles is described. Substrate scope was found to include both aryl and aliphatic N-acyl pyrroles as the Michael acceptors, and isolated product yields as high as 93% were observed. The use of acetonitrile as the reaction solvent proved to be crucial for catalysis, both to function as a labile ligand for copper, as well as an agent to minimize hydrolytic catalyst poisoning. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：833 / 836

页数：4

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