Enantioselective Synthesis of Azetidines through [3+1]-Cycloaddition of Donor-Acceptor Aziridines with Isocyanides

被引：15

作者：

Zhang, Fengcai ^{[1
]}

Sang, Xinpeng ^{[1
]}

Zhou, Yuqiao ^{[1
]}

Cao, Weidi ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 07期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC 3+2 CYCLOADDITION; MULTICOMPONENT REACTIONS; AZAOXYALLYL CATIONS; AZOMETHINE YLIDES; NATURAL-PRODUCTS; RING EXPANSION; CONSTRUCTION; ACTIVATION; REACTIVITY; CATALYSIS;

D O I：

10.1021/acs.orglett.2c00190

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective [3 + 1]-cycloaddition of racemic donor-acceptor (D-A) aziridines with isocyanides was first realized under mild reaction conditions using a chiral N,N '-dioxide/Mg-II complex as catalyst, providing a facile route to enantioenriched exo-imido azetidines with good to excellent yield (up to 99%) and enantioselectivity (up to 94% ee). An obvious chiral amplification effect was observed in this system, and an explanation was elucidated based on the experimental investigation and X-ray crystal structure of the enantiomerically pure catalyst.

引用

页码：1513 / 1517

页数：5

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