Catalytic asymmetric cyclopropanation of sulfoxonium ylides catalyzed by a chiral-at-metal rhodium complex

被引：8

作者：

Ming, Siliang ^{[1
]}

Yang, Jian ^{[1
]}

Wu, Shi ^{[1
]}

Yao, Gang ^{[1
]}

Xiong, Hongwei ^{[1
]}

Du, Yu ^{[2
]}

Gong, Jun ^{[1
]}

机构：

[1] Hubei Univ Sci & Technol, Sch Pharm, Xianning 437100, Hubei, Peoples R China

[2] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 19期

基金：

中国国家自然科学基金;

关键词：

2,2-DISUBSTITUTED TERMINAL EPOXIDES; SULFUR YLIDES; CYCLIZATION REACTIONS; MICHAEL ADDITION; EPOXIDATION; FUNCTIONALIZATION; INSERTION;

D O I：

10.1039/d2qo01068b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient asymmetric cyclopropanation of sulfoxonium ylides with alpha,beta-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal rhodium complex has been developed. The enantioenriched cyclopropane derivatives bearing three contiguous tertiary stereocenters were obtained in generally high yields (up to 98%) with excellent stereoselectivities (up to >20 : 1 dr, >99% ee). Remarkably, as low as 0.1 mol% of the chiral Rh(iii) complex can realize a scale-up reaction with excellent yield and enantioselectivity.

引用

页码：5147 / 5153

页数：7

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