Synthesis 2015; 47(11): 1581-1592
DOI: 10.1055/s-0034-1380404
paper
© Georg Thieme Verlag Stuttgart · New York

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

Yu-Long An
a  Department of Chemistry, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China   Email: syzhao8@dhu.edu.cn
,
Yun-Xia Deng
b  Department of Biological Engineering, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China
,
Wei Zhang
a  Department of Chemistry, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China   Email: syzhao8@dhu.edu.cn
,
Sheng-Yin Zhao*
a  Department of Chemistry, Donghua University, No. 2999 North Renmin Road, Shanghai 201620, P. R. of China   Email: syzhao8@dhu.edu.cn
c  State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 17 December 2014

Accepted after revision: 23 January 2015

Publication Date:
05 March 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.

Supporting Information

 
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