Tetrahedron letters

Palladium catalyzed reductive decarboxylation of allyl α-alkenyl-β-ketoesters. A new synthesis of (E)-3-alkenones

V Ragoussis, A Giannikopoulos

Index: Ragoussis, Valentine; Giannikopoulos, Alexandros Tetrahedron Letters, 2006 , vol. 47, # 5 p. 683 - 687

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Citation Number: 12

Abstract

The reductive decarboxylation of α-alkenyl derivatives of allyl-β-ketoesters was achieved by use of palladium (0) catalyst generated in situ from Pd (OAc) 2 and PPh3, with triethylammonium formate as the hydride source, in THF. The reaction proceeds smoothly and cleanly, with linear alkenyl derivatives of allyl-β-ketoesters, to afford (E)-3-alkenones in good to excellent yields (73–92%) and high stereoselectivity (> 98%).