Organic & Biomolecular Chemistry 2005-06-07

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

Kristin M Brinner, Jonathan A Ellman

Index: Org. Biomol. Chem. 3(11) , 2109-13, (2005)

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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.