Efficient synthesis of enantiomerically pure 2-acylaziridines: Facile syntheses of N-Boc-safingol, N-Boc-D-erythro-sphinganine, and N-Boc-spisulosine from a common intermediate

Jung Min Yun, Taebo Sim, Heung Sik Hahm, Won Koo Lee, Hyun Joon Ha

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Abstract

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 NaBH 4 in the presence of ZnCl 2 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.

Original languageEnglish
Pages (from-to)7675-7680
Number of pages6
JournalJournal of Organic Chemistry
Volume68
Issue number20
DOIs
Publication statusPublished - 2003 Oct 3
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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