Asymmetric Synthesis of 2-Substituted Hexahydroquinolin-4-ones Using a Pd-Catalyzed Asymmetric Allylic Amination and Intramolecular Mannich Reaction: Catalytic Asymmetric Synthesis of 2-epi-cis-195A

Abstract

A novel method of the enantioselective synthesis of 2-substitutedhexahydroquinolin-4-ones is described. The method relies on a Pd-catalyzedasymmetric allylic amination using a chiral diaminophosphine oxide(DIAPHOX) preligand and diastereoselective intramolecular Mannichreaction. The developed synthetic method could be applied to thecatalytic asymmetric synthesis of (+)-2- EPI- CIS-195A.