Efficient catalytic synthesis of optically pure 1,2-azido alcohols through enantioselective epoxide ring opening with HN 3

Abstract

Chiral binuclear Co(salen) complexes bearing Lewis acid of group 13 metal chlorides show very high catalytic activity and enantioselectivity for the ring opening of epoxides using HN 3 as azide source. It provides a facile and practical synthetic route to a wide range of chiral nonracemic 1,2-azido alcohols and related compounds in one-pot synthesis with excellent selectivity (92.0–99.6% e.e.) under mild conditions. The presence of Lewis acid of group 13 shows a strong synergistic effect.