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Synfacts 2009(1): 0059-0059  
DOI: 10.1055/s-0028-1087396
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Asymmetric Conjugate Reduction/Aldol Reaction

Contributor(s): Mark Lautens, Praew Thansandote
B. H. Lipshutz*, B. Amorelli, J. B. Unger
University of California, Santa Barbara, USA
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Publikationsdatum:
18. Dezember 2008 (online)

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Significance

Combining an asymmetric copper-catalyzed conjugate reduction with an intramolecular aldol reaction gives cyclohexane products with three contiguous stereocenters. Good yields and enantioselectivities are seen for both Z- and E-trisubstituted keto enones. Additionally, heterogeneous Cu/C can be used with the E-substrate to form the desired product. Alternatively, using Cu(OAc)2, water and the surfactant PTS with the Z-substrate, the enantiomer of the product obtained under heterogeneous condition is formed.