Asymmetric synthesis of pyrrolidinoindolines. Application for the practical total synthesis of (-)-phenserine

A Huang, JJ Kodanko, LE Overman

Index: Huang, Audris; Kodanko, Jeremy J.; Overman, Larry E. Journal of the American Chemical Society, 2004 , vol. 126, # 43 p. 14043 - 14053

Full Text: HTML

Citation Number: 151

Abstract

A versatile route to enantiopure 3, 3-disubstituted oxindoles and 3a-substituted pyrrolidinoindolines is described in which diastereoselective dialkylation of enantiopure ditriflate 10 with oxindole enolates is the central step. These reactions are rare examples of alkylations of prostereogenic enolates with chiral sp3 electrophiles that proceed with high facial selectivity (10-20: 1). The scope of this method is explored, and a model to ...