Regioselective Hetero-Michael Addition of Oxygen, Sulfur, and Nitrogen­ Nucleophiles to Maleimides Catalyzed by BF₃·OEt₂

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 etherate

• References

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