ChemInform Abstract: Stereoselective Synthesis of 4‐Amino‐2,3‐unsaturated‐N‐Cbz‐imino‐O‐glycosides via New Diastereoisomeric N‐Cbz‐Imino Glycal‐Derived Allyl N‐Nosyl Aziridines.

Abstract

Carbohydrates U 0500Stereoselective Synthesis of 4-Amino-2,3-unsaturated-N-Cbz-imino-O-glycosides via New Diastereoisomeric N-Cbz-Imino Glycal-Derived Allyl N-Nosyl Aziridines.-The reaction of (I) or (V) with alcohols proceeds via intermediate aziridines to afford the corresponding ethers with high βor α-selectivity, respectively. The products can be easily deprotected leading to the desired free amines [cf. (VIII), (IX)]. -(DI BUSSOLO*, V.; FIASELLA, A.; FAVERO, L.; BERTOLLINI, F.; CROTTI, P.; Org. Lett. 11 (2009) 12, 2675-2678; Dip. Sci. Farm., Univ. Pisa, I-56126 Pisa, Italy; Eng.) -R. Steudel 46-190