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Synthesis 2015; 47(11): 1581-1592
DOI: 10.1055/s-0034-1380404
DOI: 10.1055/s-0034-1380404
paper
Regioselective Hetero-Michael Addition of Oxygen, Sulfur, and Nitrogen Nucleophiles to Maleimides Catalyzed by BF3·OEt2
Authors
Weitere Informationen
Publikationsverlauf
Received: 17. Dezember 2014
Accepted after revision: 23. Januar 2015
Publikationsdatum:
05. März 2015 (online)
Abstract
A practical BF3·OEt2-catalyzed regioselective 1,2-addition or 1,4-hetero-Michael addition of oxygen, sulfur, and nitrogen nucleophiles to maleimides has been developed for the synthesis of alkyl fumarate derivatives or 3-substituted succinimides, respectively. This reaction system has wide substrate scope and gives moderate to excellent yields (up to 96%) of the desired products. In contrast to the base-catalyzed methods, this strategy is very general, simple, environmentally friendly, and tolerant of oxygen.
Key words
Michael addition - maleimide - oxygen nucleophiles - sulfur nucleophiles - nitrogen nucleophiles - boron trifluoride diethyl etherateSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380404.
- Supporting Information (PDF)
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