A Stereoselective Access to Cyclic cis-1,2-Amino Alcohols from trans-1,2-Azido Alcohol Precursors

Abstract

A unique one-pot synthesis of cyclic cis-1,2-amino alcohols from trans-1,2-azido alcohol precursors was developed. The key step is highlighted by the stereoselective reduction of the cyclic alpha-alkoxy imines, which could be prepared from the corresponding azides by ruthenium catalysis under photolytic conditions. Remarkably, this unprecedented reaction pathway offers a stereodivergent access to structurally diverse cyclic 1,2-amino alcohols.