Regiocontrol of the palladium-catalyzed tin hydride addition to Z-enynols: remarkable Z-directing effects.
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.
Hamze
Abdallah
A
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.
Provot
Olivier
O
Brion
Jean-Daniel
JD
Alami
Mouâd
M
D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D017971:Tin Compounds / Q000737:chemistry*
D009947:Organotin Compounds; D017971:Tin Compounds; C510267:hydrostannane; D010165:Palladium; D002244:Carbon; D006859:Hydrogen