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Synfacts 2008(6): 0596-0596  
DOI: 10.1055/s-2008-1072618
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Reductive Aldol Reaction of Vinyl Ketones

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
C. Bee, S. B. Han, A. Hassan, H. Iida, M. J. Krische*
University of Texas at Austin, USA
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Publication History

Publication Date:
21 May 2008 (online)

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Significance

The authors report the first enantio­selective reductive aldol coupling of vinyl ketones, which were achieved through the design of a new class of TADDOL-like phosphonite ligands (AP I - AP IV). Hydrogenation of commercially available methyl vinyl ketone or ethyl vinyl ketone in the presence of aldehydes using cationic rhodium catalysts modified by chiral phosphonite ligands produces aldol adducts with excellent control of relative and absolute stereochemistry.