Asymmetric Functionalization of Bicycloalkenes by Catalytic Enantioposition-Selective Hydrosilylation

Article abstract of DOI:10.1016/S0040-4039(00)60868-7

Hydrosilylation of norbornene with trichlorosilane in the presence of palladium catalyst (0.01-0.1 mol percent) coordinated with (R)-MOP ligand gave a quantitative yield of exo-2-trichlorosilylnorbornane, which was oxidized with hydrogen peroxide to give (1S,2S,4R)-exo-2-norbornanol in 96percent ee.The similar hydrosilylation and oxidation of endo-5,6-dicarbomethoxy-2-norbornene, bicyclo<2.2.2>octene, and norbornadiene gave the corresponding bicyclic alcohols of 94percent ee, 92percent ee, and 95percent ee, respectively.