Journal
TETRAHEDRON
Volume 64, Issue 51, Pages 11697-11705Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.10.007
Keywords
Vinylogous Michael reaction; 1,4-Addition reaction; Pyrrolin-2-ones; 4-Methoxytetramates
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Funding
- Universita di Parma
- Centro Interdisciplinare di Studi Bio-Molecolari e Applicazioni Inclustriali (CISI, Milano, Italy)
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The direct Mukaiyama-Michael addition of vinylogous tetramate donors to a number of different Michael acceptors has been easily executed, by employing the TMSOTf/Et3N Mixture as soft Lewis acid/base promoter agent. Richly functionalized, highly manipulable gamma-substituted pyrrolinone products were practically synthesized in acceptable to excellent yields, and with diastereoselectivities heavily relying upon the substituent at the nitrogen atom of the pyrrolinone donor. (C) 2008 Elsevier Ltd. All rights reserved.
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