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

页码：509 / 512

页数：5

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