A copper(II)-catalyzed, sequential Michael-aldol reaction for the preparation of 1,2-dihydroquinolines
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- 作者：Anna M. Wagner awenzel@kecksci.claremont.edu ; Claire E. Knezevic ; Jessica L. Wall ; Victoria L. Sun ; Joshua A. Buss ; LeeAnn T. Allen ; Anna G. Wenzel
- 关键词：Heterocycles ; Lewis acid catalysis ; Michael&ndash ; aldol reaction ; Acetonitrile ; Small-molecule synthesis
- 刊名：Tetrahedron Letters
- 出版年：2012
- 出版时间：15 February, 2012
- 年：2012
- 卷：53
- 期：7
- 页码：833-836
- 全文大小：325 K
文摘
A copper(II)-catalyzed, sequential Michael addition-aldol condensation reaction of N-carboxybenzyl-protected aminobenzaldehyde with various ¦Á,¦Â-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.