A Versatile Route to (<i>E</i>)- and (<i>Z</i>)-2-Hydroxy-3,4-unsaturated Disubstituted Sulfilimines and Their Haloamidation Reaction

Abstract

Alpha-chloro ynones have been reduced using Noyori's Ru catalyst to furnish alpha-chloro propargylic alcohols with excellent enantioselectivity. These have been used as a common precursor for the preparation of (E)- and (Z)-2-hydroxy-3,4-unsaturated disubstituted sulfilimines. The latter serve as precursors for the highly regio- and stereoselective preparation of bromo carbamates.