Stereoselective synthesis of α-(dichloromethyl)amines, α-(chloromethyl)amines, and α-chloroaziridines

被引：17

作者：

Li, Desheng ^{[1
]}

Li, Ya ^{[1
]}

Chen, Zhiqiu ^{[1
]}

Shang, Huaqi ^{[1
]}

Li, Hongsen ^{[1
]}

Ren, Xinfeng ^{[1
]}

机构：

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

来源：

RSC ADVANCES | 2014年 / 4卷 / 27期

基金：

中国国家自然科学基金;

关键词：

HALOGENATED IMINO COMPOUNDS; CHIRAL N-ACYLHYDRAZONES; ASYMMETRIC-SYNTHESIS; RADICAL-ADDITION; FACILE SYNTHESIS; FUNCTIONALIZED AZIRIDINES; STEREOSPECIFIC SYNTHESIS; ACID-CHLORIDES; REDUCTION; REARRANGEMENT;

D O I：

10.1039/c4ra00471j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Protocols for the stereoselective synthesis of alpha-(dichloromethyl)amines, alpha-(chloromethyl)amines, and alpha-chloroaziridines are presented. Diastereoselective synthesis of alpha-(dichloromethyl)amines was achieved based on nucleophilic dichloromethylation of aromatic N-tert-butylsulfinyl aldimines with (dichloromethyl)trimethylsilane at a low reaction temperature. Slowly warming the reaction mixture up to room temperature gave alpha-chloro cis-aziridines. Additionally, with Bu3SnH as the reductant, alpha-(dichloromethyl)amines were readily obtained from easily accessible alpha-(trichloromethyl)amines via mono-dechlorination. Over-reduction was successfully suppressed. Subsequent radical mono-dechlorination of the alpha-(dichloromethyl)amines gave the corresponding alpha-(chloromethyl)amines in good to excellent yields.

引用

页码：14254 / 14263

页数：10

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