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

被引：20
|
作者：
An, Yu-Long [1 ]
Deng, Yun-Xia [2 ]
Zhang, Wei [1 ]
Zhao, Sheng-Yin [1 ,3 ]
机构：
[1] Donghua Univ, Dept Chem, Shanghai 201620, Peoples R China
[2] Donghua Univ, Dept Biol Engn, Shanghai 201620, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 11期
基金：
中国国家自然科学基金;
关键词：
Michael addition; maleimide; oxygen nucleophiles; sulfur nucleophiles; nitrogen nucleophiles; boron trifluoride diethyl etherate; ALPHA; BETA-ETHYLENIC COMPOUNDS; ALPHA-CHLOROSUCCINIMIDES; SUCCINIMIDE DERIVATIVES; ULTRASOUND ACTIVATION; CONJUGATE ADDITION; RING EXPANSION; AMINES; BASE; ACIDS; CYCLIZATION;
D O I：
10.1055/s-0034-1380404
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical BF3 center dot 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.
引用
收藏
页码：1581 / 1592
页数：12
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