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

Author:

An Yu-Long1,Deng Yun-Xia2,Zhang Wei1,Zhao Sheng-Yin13

Affiliation:

1. Department of Chemistry, Donghua University

2. Department of Biological Engineering, Donghua University

3. State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

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.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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