Enantioselective synthesis of homoallylic amines by addition of allylmetal reagents to imines derived from (S)-valine esters

…, A Bocoum, D Savoia, A Umani-Ronchi

Index: Basile, Tiziana; Bocoum, Allaye; Savoia, Diego; Umani-Ronchi, Achille Journal of Organic Chemistry, 1994 , vol. 59, # 25 p. 7766 - 7773

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Citation Number: 135

Abstract

Grignard and Barbier procedures have been applied to the addition of allylmetal (Zn, Cu, Pb, Bi, Al, In) species to imines derived from@)-valine esters, principally the methyl ester. The Zn- mediated, CeC13-or SnClz-catalyzed" Barbier" reactions of the imines with allyl bromide in THF in Ar atmosphere at room temperature proved particularly convenient, efficient and selective, providing the secondary homoallylic amines with excellent to perfect ...