Allyltrimethylsilane, palladium-catalyzed

Yamamoto reported the first palladium catalyzed addition of allyltributyltin or allyltrimethylsilane to N benzyl imines [94]. Higher enantioselectivities are obtained if the reaction is performed in the presence of 1 equiv of water (Scheme 1.24). 

The palladium-catalyzed [3+2] cycloaddition reaction between enantiomerically pure a,P-unsaturated sulfoxides and trimethylenemethane (266), using the methodology developed by Trost [198], has been reported [199]. Thus, reaction of the sulfoxide (31), 2-acetoxymethyl-3-allyltrimethylsilane (2eq), palladium acetate (5mol%), and triisopropylphosphite (20 eq) in THF under reflux gave the major cycloadduct (267) in 80% yield and 80% de (Scheme 5.87). Moderate to good levels of asymmetric induction were observed for various a,P unsaturated sulfoxides. 

Palladium acetate associated with DPPP (diphenylphosphinopropane) [G4CiIm]BF4 catalyze the regioselective Heck arylation of electron-rich olefins-vinyl ethers, enamides, and allyltrimethylsilanes (Scheme 37). ... 

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