Regio-and stereoselectivity control in palladium-catalyzed allylic alkylation of 1-cycloalkenylmethyl acetates

O Jacquet, JY Legros, M Coliboeuf, JC Fiaud

Index: Jacquet, Olivier; Legros, Jean-Yves; Coliboeuf, Matthieu; Fiaud, Jean-Claude Tetrahedron, 2008 , vol. 64, # 27 p. 6530 - 6536

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Citation Number: 10

Abstract

Enantiomerically pure allylic acetates 1a and 1b were obtained by lipase-catalyzed acylation through kinetic resolution processes of the racemates. Palladium-catalyzed alkylation of 1a with dimethyl malonate was both regio-and stereoselective, showing that no isomerization of the acetate 1a or the intermediate π-allylic palladium complex took place under the conditions used. Alkylation of 1b was stereoselective but not regioselective. The ...