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: norbert.dekimpeugent.be

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

DOI: 10.1021/jo0624795

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Abstract

Reduction of (R_S)-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 (R_S,S)-N-(tert-butylsulfinyl)aziridines in quantitative yields. On the contrary, its epimer, (R_S,R)-N-(tert-butylsulfinyl)aziridine was synthesized in good yields and diastereoselectivity by switchover of the reducing agent from NaBH₄ to LiBHEt₃.

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Key Words

De Kimpe Aziridine Synthesis, Sodium Borohydride, Lithium Triethylborohydride

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ID: J42-Y2007-4220