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Synfacts 2008(9): 0946-0946  
DOI: 10.1055/s-2008-1078000
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Michael Reaction of Keto Esters with Camphor-Derived Acrylate

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
C. Palomo*, M. Oiarbide, J. M. Garcia, P. Banuelos, J. M. Odriozola, J. Razkin, A. Linden
Universidad del Pais Vasco, San Sebastian and Universidad Publica de Navarra, Pamplona, Spain; University of Zurich, Switzerland
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Publikationsdatum:
22. August 2008 (online)

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Significance

Asymmetric conjugate addition reactions using soft carbon nucleophiles are well known as an efficient means to generate all-carbon stereocenters. Despite the wealth of literature in this field, relatively few examples exist for conjugate addition to acrylate acceptors. The authors report that use of camphor-derived a′-hydroxy enone (for use in the Diels-Alder reaction, see: C. Palomo et al. J. Am. Chem. Soc. 2002, 124, 10288) as a chiral auxiliary in concert with cata­lytic Cu(TfO)2 catalyzes the conjugate addition of various cyclic and acyclic keto esters in high yields and diastereomeric ratios.