Organic Chemistry Portal



Asymmetric Synthesis of Aziridines by Reduction of N-tert-Butanesulfinyl α-Chloro Imines

Bram Denolf, Erika Leemans and Norbert De Kimpe*

*Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium, Email:

B. Denolf, E. Leemans, N. De Kimpe, J. Org. Chem., 2007, 72, 3211-3217.

DOI: 10.1021/jo0624795

see article for more reactions


Reduction of (RS)-N-tert-butanesulfinyl α-halo imines with NaBH4 in THF, in the presence of 10 equiv of MeOH, and subsequent cyclization with KOH afforded the corresponding (RS,S)-N-(tert-butylsulfinyl)aziridines in quantitative yields. On the contrary, its epimer, (RS,R)-N-(tert-butylsulfinyl)aziridine was synthesized in good yields and diastereoselectivity by switchover of the reducing agent from NaBH4 to LiBHEt3.

see article for more examples

Key Words

De Kimpe Aziridine Synthesis, Sodium Borohydride, Lithium Triethylborohydride

ID: J42-Y2007-4220