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

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• 作者：Abdallah Hamze ; Olivier Provot ; Jean-Daniel Brion ; Mouâ ; d Alami
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：May 11, 2007
• 年：2007
• 卷：72
• 期：10
• 页码：3868 - 3874
• 全文大小：208K
• 年卷期：v.72,no.10(May 11, 2007)
• ISSN：1520-6904

文摘

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Palladium-catalyzed hydrostannation of substituted Z- and E-enynols is discussed and compared. Theregioselectivity of the H-Sn bond addition was found to be controlled by the geometry of the doublebond (Z- or syn-directing effect) rather than the nature of its substituents. Exclusively -vinyl stannaneswere obtained from Z-enynols having various substituents on the double bond regardless of their electronic,steric, or chelating natures.