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

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 PPh 3, with triethylammonium formate as the hydride source, in THF. The reaction proceeds smoothly and cleanly, with linear alkenyl derivativ...

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Bibliographic Details
Published in:Tetrahedron letters 2006-01, Vol.47 (5), p.683-687
Main Authors: Ragoussis, Valentine, Giannikopoulos, Alexandros
Format: Article
Language:English
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Summary: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 PPh 3, 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%).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.11.122