Highly Stereoselective and Practical Synthesis of a-Trichloromethyl Amines and 2,2-Dichloroaziridines from Chloroform

被引：27

作者：

Li, Ya ^{[1
,2
]}

Zheng, Tao ^{[1
]}

Wang, Wei ^{[1
]}

Xu, Wei ^{[3
]}

Ma, Yingchao ^{[1
]}

Zhang, Sishi ^{[1
]}

Wang, Han ^{[1
]}

Sun, Zhihua ^{[1
]}

机构：

[1] Shanghai Univ Engn Sci, Coll Chem & Chem Engn, Shanghai 201620, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[3] Texas A&M Univ, Dept Biol, College Stn, TX 77843 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 2-3期

基金：

中国国家自然科学基金;

关键词：

chloroform; dichloroaziridines; imines; a-trichloromethyl amines; trichloromethyl substituents; MANNICH-TYPE REACTIONS; KETENE SILYL ACETALS; RADICAL HALOALKYLATION; BARBAMIDE BIOSYNTHESIS; GEM-DICHLOROAZIRIDINES; ASYMMETRIC-SYNTHESIS; DYSIDEA-HERBACEA; BETA-SULTAMS; DERIVATIVES; CONVENIENT;

D O I：

10.1002/adsc.201100713

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A highly stereoselective and practical synthesis of a-trichloromethyl amines by nucleophilic trichloromethylation of N-(tert-butylsulfinyl)imines with chloroform was achieved. The obtained a-trichloromethyl amines can be further transformed into chiral 2,2-dichloroaziridines through an intramolecular nucleophilic substitution methodology. 2,2-Dichloroaziridines can also be produced directly from chloroform and N-(tert-butylsulfinyl)imines through a one-pot procedure.

引用

页码：308 / 312

页数：5

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