A Ruthenium-Catalyzed One-Pot α-Alkylation of Ketones with Aldehydes

C. S. Cho; S. C. Shim

doi:10.1055/s-2006-955807

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Synfacts 2007(2): 0201-0201
DOI: 10.1055/s-2006-955807

Metal-Mediated Synthesis

A Ruthenium-Catalyzed One-Pot α-Alkylation of Ketones with Aldehydes

Contributor(s): Paul Knochel, Andrei Gavryushin
C. S. Cho*, S. C. Shim*
Kyungpook National University, Daegu, Korea

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Publication History

Publication Date:
23 January 2007 (online)

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Significance

This work concerns the Ru-catalyzed α-alkylation of ketones and secondary alcohols via a cascade of condensation and transfer hydrogenation. This method offers a simple one-pot alternative to the condensation-reduction sequence, leading to formal products of a ketone alkylation. Rather unusually, dioxane serves as a hydrogen donor in this process. The double bond of benzylidene acetophenone is reduced by dioxane in the presence of Ru(PPh₃)₂Cl₂. This reaction may also serve as a simple method for the reduction of enones.