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We herein report an effective hydrosilylation of 1,1-disubstituted allenes with a palladium catalyst modified by a monophosphorus ligand, leading to a series of α-tertiary allylsilanes in high yields and exceptional regioselectivities. The employment of BI-DIME is essential for the high reactivities and selectivities. A chiral α-tertiary allylsilane is formed in excellent ee for the first time by employing a chiral monophosphorus ligand.