Lewis Base-Promoted Hydrosilylation of Cyclic Malonates: Synthesis of β-Substituted Aldehydes and γ-Substituted Amines

The Lewis base-promoted hydrosilylation of cyclic malonates provides a convenient synthesis of beta-substituted aldehydes. No over-reduction to the primary alcohol is observed as the aldehyde functionality is protected until a subsequent hydrolysis step. The utility of the method is demonstrated in a number of examples and further in the synthesis of gamma-substituted propylamines in a one-pot hydrosilylation/reductive amination process.