Gribble, Michael W.
Pirnot, Michael T.
Bandar, Jeffrey S.
Liu, Richard Y.
Buchwald, Stephen L.

Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles

“,
J. Am. Chem. Soc
,
2017
,
139
(
6
)
,
2192-2195
.
Abstract

We report a highly enantioselective CuH- catalyzed Markovnikov hydrosilylation of vinylarenes and vinyl heterocycles. This method has a broad scope and enables both the synthesis of isolable silanes and the conversion of crude products to chiral alcohols. Density functional theory calculations support a mechanism proceeding by hydrocupration followed by σ-bond meta- thesis with a hydrosilane.