Novel Synthesis of Chiral Unactivated 2-Aryl-1-benzylaziridines

被引：26

作者：

Leemans, Erika ^{[1
]}

Mangelinckx, Sven ^{[1
]}

De Kimpe, Norbert ^{[1
]}

机构：

[1] Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

来源：

SYNLETT | 2009年 / 08期

关键词：

chiral aziridines; asymmetric synthesis; ring opening; ring closure; haloimines; ASYMMETRIC AZIRIDINE SYNTHESIS; AZA-DARZENS REACTION; PHENYLETHYLAMINE ALPHA-PEA; BETA-HYDROXY AMINES; ENANTIOSELECTIVE SYNTHESIS; N-DIPHENYLPHOSPHINYLIMINES; TRANSFER HYDROGENATION; ENANTIOPURE COMPOUNDS; RADICAL ADDITIONS; PART;

D O I：

10.1055/s-0028-1088125

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral (R-S,R)- and (R-S,S)-N-(tert-butylsulfinyl)-2-aryl-aziridines were transformed into (R)- and (S)-2-aryl-1-benzylaziridines via a short three-step procedure. Deprotection and ring opening of (R-S,R)- and (R-S,S)-N-sulfinyl-2-arylaziridines (95-99% de) in acid medium afforded 2-aryl-2-chloroethylamine hydrochlorides in high yield (83-90%). These intermediates were converted into the corresponding chiral N-(benzylidene)-beta-aryl-beta-chloro-amines in good yield (78-85%). Subsequent reduction of the synthesized aldimines afforded chiral 2-aryl-1-benzylaziridines in good to excellent yield (74-94%) and enantiomeric excess (83-99% ee). The enantiomeric purity of the chiral aldimines and aziridines was established by NMR spectroscopy using Pirkle alcohol as the chiral solvating agent.

引用

页码：1265 / 1268

页数：4

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