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  • Regiocontrol of the palladium-catalyzed tin hydride addition to Z-enynols: remarkable Z-directing effects.

Regiocontrol of the palladium-catalyzed tin hydride addition to Z-enynols: remarkable Z-directing effects.

The Journal of organic chemistry (2007-04-17)
Abdallah Hamze, Olivier Provot, Jean-Daniel Brion, Mouâd Alami
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 alpha-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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tert-Butylmagnesium chloride solution, 2.0 M in diethyl ether