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
收藏
页码：14254 / 14263
页数：10
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