Stereospecific Synthesis Of N-Acyl-(E)-Vinyl-, Dienyl-, And Enynylsulfoximines

Robert S. Paley, Swarthmore College
S. R. Snow

Abstract

A β-tosylvinylsulfoximine, , was used as the common starting point for the preparation of the title compounds. Treatment of with “higher-order cuprates” or trialkylalanes (with a Pd(II) catalyst) afforded NTBDMS-(E)-vinylsulfoximines, whereas dienylsulfoximines and enynylsulfoximines were obtained by treatment with divinylalanes and alkynylalanes in a Pd(0)-catalyzed process. The N-pivaloyl derivative of each sulfoximine was readily prepared.