A regio- and stereodivergent synthesis of vic-amino alcohols

Org Lett. 2000 Dec 14;2(25):4087-9. doi: 10.1021/ol006736i.

Abstract

A regio- and stereodivergent synthesis of vic-amino alcohols starting from vinylepoxides is described. The developed strategy focuses on the propensity of vinylepoxides and vinylaziridines to be ring-opened at the allylic position by suitable nucleophiles and makes use of reactions that perform such tasks selectively with either retention or inversion of configuration.