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.
J Org Chem
; 68(20): 7675-80, 2003 Oct 03.
Article
en En
| MEDLINE
| ID: mdl-14510541
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 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.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Esfingosina
/
Aziridinas
/
Lípidos
Idioma:
En
Revista:
J Org Chem
Año:
2003
Tipo del documento:
Article