Regio- and Stereoselective Ring-Opening Reaction of Chiral Aziridines: A Facile Synthesis of Chiral β-Amino Alcohols

Abstract

The reaction of chiral 2-alkylsubstituted aziridines (1a-d) with acetic acid afforded β-amino alcohols with an (S)-chiral center at the β position (with respect to oxygen). In contrast, a reaction of the same chiral aziridines with acetyl chloride followed by treatment with water gave β-amino alcohols that have an (S)-chiral center at the a position. In addition, the reaction of the same chiral aziridines with benzyl bromide followed by treatment with 2% sulfuric acid gave the β-amino alcohols with an (R)-chiral center at the a position. Thus, we could control the regioselectivity and stereoselectivity of the ring-opening reaction of chiral aziridines (1a-d).