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Synfacts 2006(5): 0460-0460
DOI: 10.1055/s-2006-934441
DOI: 10.1055/s-2006-934441
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Hydrogen-Mediated Aldol Reductive Coupling of Vinyl Ketones
C. Jung, S. A. Garner, M. J. Krische*
University of Texas at Austin, USA
Further Information
Publication History
Publication Date:
21 April 2006 (online)
Significance
The reductive aldol coupling of vinyl ketones with a variety of aldehydes was accomplished. The reaction proceeded with high yields and diastereoselectivities. The use of (2-Fur)3P as phosphine ligand was shown to dramatically increase the diastereoselectivity compared to Ph3P (19:1 vs 3:1). One very nice feature of this protocol is the use of only 1 atm of H2 (balloon) that was needed as the reductant. H2-labile functional groups (i.e. benzyl ethers, alkenes and alkynes) remain intact under the reaction conditions.