Creating Stereocenters within Acyclic Systems by C-C Bond Cleavage of Cyclopropanes

被引：154

作者：

Cohen, Yair ^{[1
]}

Cohen, Anthony ^{[1
]}

Marek, Ilan ^{[1
]}

机构：

[1] Technion Israel Inst Technol, Schulich Fac Chem, IL-3200009 Haifa, Israel

来源：

CHEMICAL REVIEWS | 2021年 / 121卷 / 01期

基金：

以色列科学基金会;

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; QUATERNARY STEREOGENIC CENTERS; PARA-QUINONE METHIDES; ORGANIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; REMOTE FUNCTIONALIZATION; HECK ARYLATIONS; ENANTIOSELECTIVE SYNTHESIS; ACTIVATED CYCLOPROPANES; BROOK REARRANGEMENT;

D O I：

10.1021/acs.chemrev.0c00167

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Recent developments in the stereoselective synthesis of polysubstituted cyclopropanes nowadays allow chemists to easily access these strained rings with high diastereo- and enantiomeric ratios. In turn, this development has created a paradigm shift for the synthesis of stereodefined acyclic molecules though selective carbon-carbon bond cleavage. Through chosen illustrative examples, we aim to show in this review that the cleavage of cyclopropane is a powerful approach to reveal sp(3) stereocenters in acyclic systems. The application of these concepts was illustrated by the total syntheses of several natural products and other important molecules, further showing the power of these strategies as a powerful tool in organic synthesis.

引用

页码：140 / 161

页数：22

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