Reversal of regioselectivity in reactions of donor-acceptor cyclopropanes with electrophilic olefins

被引：12
|
作者：
Turkowska, Joanna [1 ]
Durka, Jakub [1 ]
Ociepa, Michal [1 ]
Gryko, Dorota [1 ]
机构：
[1] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland
来源：
CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 04期
关键词：
ELECTROCHEMICAL REACTIONS; VITAMIN-B-12; DERIVATIVES; REARRANGEMENT; CATALYSIS; LACTONES; STRAIN;
D O I：
10.1039/d1cc05330b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reactivity of donor-acceptor cyclopropanes towards nucleophiles and electrophiles is determined by the specific philicity of the carbon atoms originating from the strong polarization of the central C-C bond. Herein, we report that vitamin B-12 catalysis enables the transformation of an initially electrophilic center into a nucleophilic radical that reacts with SOMOphiles. This radical-based strategy reverses the standard regioselectivity and thus complements the classical approaches.
引用
收藏
页码：509 / 512
页数：5
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