Various enantiomerically pure 2-acylaziridines were prepared efficiently from the corresponding aziridine-2-carboxylate via Weinreb's amide and the subsequent treatment of organometallic compounds. The carbonyl group of those 2-acylaziridines was stereoselectively reduced by NaBH4in the presence of ZnCl2 to give erythro-1,2-amino alcohols with high diastereoselectivities and chemical yields. Using this methodology, we prepared (1R,2S)-N-Boc-norephedrine 5, N-Boc-safingol 8, N-Boc-D-erythro-sphinganine 9, and N-Boc-spisulosine 10 in high yields.

Intermediate. -Treatment of ester (I) with the hydroxylamine (II) followed by reaction with organometallic compounds offers an efficient approach to enantiomerically pure 2-acylaziridines. In the presence of NaBH4/ZnCl2 or L-Selectride, the latter undergo highly diastereoselective reduction to afford erythroor threo-1,2-amino alcohols. Using this method, facile synthesis of the title compounds (VIIIa), (X), and (XII) is possible. -(YUN, J. M.; SIM, T. B.; HAHM, H. S.; LEE*, W. K.; HA, H.-J.; J.

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