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.alami
u-psud.fr
A. Hamze, O. Provot, J.-D. Brion, M. Alami, J. Org. Chem., 2007, 72, 3868-3874.
DOI: 10.1021/jo0701435 (free Supporting Information)
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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
ID: J42-Y2007-1430
