ASYMMETRIC INTRAMOLECULAR AMIDATION OF N-(TERT-BUTOXYCARBONYL)-3-HYDROXY-4-PENTENYLAMINE - A NEW ENTRY TO CHIRAL BUILDING-BLOCKS FOR THE SYNTHESIS OF BIOLOGICALLY-ACTIVE NITROGEN-CONTAINING COMPOUNDS

Sharpless reaction of racemic N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine (1) leads to both an asymmetric kinetic resolution to provide optically active 1, which was subsequently used for intramolecular amidomercuration, and asymmetric epoxidation followed by concomitant cyclization into optically active cis-3-hydroxy-2-(hydroxymethyl)pyrrolidine (3). Optically active 1 and 3 have been expediently used as chiral building blocks in the asymmetric synthesis of several biologically active natural products.