1-Hydrosilatrane: A Locomotive for Efficient Ketone Reductions

An efficient method for the reduction of ketones with 1-hydrosilatrane is described. In the presence of a Lewis base activator, the resulting secondary alcohols are rapidly formed in good to excellent yields (20 examples, 71-99% yields). The relative bulkiness of 1-hydrosilatrane also enables the diastereoselective reduction of (-)-menthone to (+)-neomenthol, and the use of a chiral alkoxide activator can lead to the enantioselective reduction of prochiral ketones.