The Journal of organic chemistry

Lewis base-promoted hydrosilylation of cyclic malonates: Synthesis of β-substituted aldehydes and γ-substituted amines

CG Frost, BC Hartley

Index: Frost, Christopher G.; Hartley, Benjamin C. Journal of Organic Chemistry, 2009 , vol. 74, # 9 p. 3599 - 3602

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Citation Number: 18

Abstract

The Lewis base-promoted hydrosilylation of cyclic malonates provides a convenient synthesis of β-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 γ- substituted propylamines in a one-pot hydrosilylation/reductive amination process.