A Tandem Organocatalytic α-Chlorination–Aldol Reaction That Proceeds with Dynamic Kinetic Resolution: A Powerful Tool for Carbohydrate Synthesis

Abstract

A tandem, proline-catalyzed α-chlorination/aldol reaction is described that involves a dynamic kinetic resolution of α-chloroaldehyde intermediates. The resulting syn-chlorohydrins are produced with good to excellent diastereoselectivity in high enantiopurity and provide new opportunities for the synthesis of carbohydrates.