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Hydrogen-Mediated Aldol Reductive Coupling of Vinyl Ketones Catalyzed by Rhodium: High Syn-Selectivity through the Effect of Tri-2-furylphosphine

Cheol-Kyu Jung, Susan A. Garner and Michael J. Krische*

*University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, Email:

C.-K. Jung, S. A. Garner, M. J. Krische, Org. Lett., 2006, 8, 519-522.

DOI: 10.1021/ol052859x (free Supporting Information)


Rhodium-catalyzed catalytic hydrogenation of methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) in the presence of various aldehydes at ambient temperature and pressure using tri-2-furylphosphine as ligand enables formation of aldol products with high levels of syn-diastereoselectivity. Hydrogen-labile functional groups, including alkynes, alkenes, benzylic ethers, and nitroarenes, remain intact under the coupling conditions.

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Key Words

2-Hydroxy Ketones

ID: J54-Y2006-470