Chiral Phosphoric Acid Catalyzed Asymmetric Addition of 2-(Vinyloxy)ethanol to Imines and Applications of the Products.

Abstract

Chiral nitrogen-containing molecules such as chiral amines, azetidines, and 2-substituted tetrahydroquinolines are important privileged scaffolds in medicinal chemistry. In this paper, an efficient and highly enantioselective chiral phosphoric acid catalyzed asymmetric addition of 2-(vinyloxy)ethanol to imines has been developed for the first time, providing the corresponding chiral amines containing dioxolane acetals that can transform into useful chiral N-heterocycles including azetidines and 2-substituted tetrahydroquinolines with excellent optical purity.