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  • Title: Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: high syn-selectivity through the effect of tri-2-furylphosphine.
    Author: Jung CK, Garner SA, Krische MJ.
    Journal: Org Lett; 2006 Feb 02; 8(3):519-22. PubMed ID: 16435874.
    Abstract:
    [reaction: see text]. Catalytic hydrogenation of methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) in the presence of diverse aldehydes at ambient temperature and pressure using tri-2-furylphosphine-ligated rhodium catalysts enables formation of aldol products with high levels of syn-diastereoselectivity. A progressive increase in diastereoselectivity is observed upon sequential replacement of phenyl residues for 2-furyl residues (Ph3P, FurPh2P, Fur2PhP, Fur3P). Hydrogen-labile functional groups, including alkynes, alkenes, benzylic ethers, and nitroarenes, remain intact under the coupling conditions.
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