Organic & biomolecular chemistry

A rapid and general method for the asymmetric synthesis of 2-substituted pyrrolidines using tert-butanesulfinamide

KM Brinner, JA Ellman

Index: Brinner, Kristin M.; Ellman, Jonathan A. Organic and Biomolecular Chemistry, 2005 , vol. 3, # 11 p. 2109 - 2113

Full Text: HTML

Citation Number: 53

Abstract

A new method for the asymmetric synthesis of 2-substituted pyrrolidines in three steps from commercially available starting materials is described. Addition of the Grignard reagent prepared from 2-(2-bromoethyl)-1, 3-dioxane to N-tert-butanesulfinyl aldimines proceeds in high yields and with good diastereoselectivities. The sulfinamide products are then cleanly converted into pyrrolidines in one step.