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

Reference:

Frost, C. G. and Hartley, B. C., 2009. Lewis Base-Promoted Hydrosilylation of Cyclic Malonates: Synthesis of β-Substituted Aldehydes and γ-Substituted Amines. The Journal of Organic Chemistry, 74 (9), pp. 3599-3602.

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Official URL:

http://dx.doi.org/10.1021/jo900390d

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.

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