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Article

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

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

Univ Paris-Sud, and CNRS, BioCIS UMR 8076, Laboratoire de Chimie Thrapeutique, Facult de Pharmacie, 5 rue J.-B. Clment, Chtenay-Malabry, F-92296, France

J. Org. Chem., 2007, 72 (10), pp 3868–3874

DOI: 10.1021/jo0701435

Publication Date (Web): April 14, 2007

†

Univ Paris-Sud.

‡

CNRS.

Author to whom correspondence should be addressed. Fax: 33(0)1.46. 83.58.28.

, mouad.alami@u-psud.fr

Abstract

Palladium-catalyzed hydrostannation of substituted Z- and E-enynols is discussed and compared. The regioselectivity of the H−Sn bond addition was found to be 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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Published In Issue May 11, 2007
Received January 24, 2007

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Article

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

Abstract

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Recommend & Share

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