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Regiocontrol of the Palladium-Catalyzed Tin Hydride Addition to Z-Enynols: Remarkable Z-Directing Effects

Abdallah Hamze, Olivier Provot, Jean-Daniel Brion and Mouâd Alami*

*Univ Paris-Sud, and CNRS, BioCIS UMR 8076, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, F-92296, France, Email: mouad.alamiu-psud.fr

A. Hamze, O. Provot, J.-D. Brion, M. Alami, J. Org. Chem., 2007, 72, 3868-3874.

DOI: 10.1021/jo0701435


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Abstract

Palladium-catalyzed hydrostannation of substituted Z- and E-enynols is controlled by the geometry of the double bond (Z- or syn-directing effect) rather than the nature of its substituents. Exclusively α-vinyl stannanes were obtained from Z-enynols having various substituents on the double bond regardless of their electronic, steric, or chelating natures.

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Key Words

Vinyl Stannanes


ID: J42-Y2007-1430