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
收藏
页码：833 / 836
页数：4
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