Molybdenum-Catalyzed Asymmetric Allylation of 3-Alkyloxindoles:  Application to the Formal Total Synthesis of (−)-Physostigmine

This method provides expedited access to (-)-physostigmine and its analogues and a variety of 3-alkyl oxindoles can be alkylated with high yields and enantioselectivity.

Abstract

The first example of Mo-catalyzed asymmetric allylation for the generation of quaternary stereocenters at a prochiral nucleophile is reported. A variety of 3-alkyl oxindoles can be alkylated with high yields and enantioselectivity. This method provides expedited access to (-)-physostigmine and its analogues.