Asymmetric synthesis of aziridines by reduction of N-tert-butanesulfinyl α-chloro imines

被引：70

作者：

Denolf, Bram ^{[1
]}

Leemans, Erika ^{[1
]}

De Kimpe, Norbert ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 09期

关键词：

D O I：

10.1021/jo0624795

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reduction of (R-S)-N-tert-butanesulfinyl alpha-halo imines afforded chiral aziridines in good to excellent yields. Upon reduction of (R-S)-N-tert-butanesulfinyl alpha-halo imines with NaBH4 in THF, in the presence of 10 equiv of MeOH, (R-S,S)-beta-halo sulfinamides were formed in excellent yield (up to 98%) with very good stereoselectivity (> 98:2). Simple treatment of the latter (R-S,S)-beta-halo-tert-butanesulfinamides with KOH afforded the corresponding (R-S,S)-N-(tert-butylsulfinyl)aziridines in quantitative yields. On the contrary, its epimer, (R-S,R)-N-(tert-butylsulfinyl)aziridine was synthesized by switchover of the reducing agent from NaBH4 to LiBHEt3. (R-S,R)-N-(tert-Butylsulfinyl)aziridines were synthesized in good yields (up to 85%) and diastereoselectivity (up to 92:8) by reduction of (R-S)-N-tert-butanesulfinyl alpha-halo imines with LiBHEt3 in dry THF and subsequent treatment with KOH. All chiral aziridines were obtained as a single diastereomer after recrystallization (overall yield up to 91%) or after flash chromatography.

引用

页码：3211 / 3217

页数：7

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