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.
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.
D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D002614:Chelating Agents / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010665:Phenylpropanolamine / Q000737:chemistry; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001388:Aziridines; D002614:Chelating Agents; D007659:Ketones; D008055:Lipids; D010665:Phenylpropanolamine; D013110:Sphingosine; C005682:safingol; C408363:spisulosine