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Synthesis 1992; 1992(1/2): 127-131
DOI: 10.1055/s-1992-34179
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Complementary Facial Selectivity in Conjugate Additions to γ-Hydroxyenones

Kevin A. Swiss* , William Hinkley, Cynthia A. Maryanoff, Dennis C. Liotta
  • *Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA
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Publication Date:
18 September 2002 (online)

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Complementary facial selectivity can be achieved in conjugate additions to γ-hydroxyenones by using either Grignard reagents or cuprates. In the case of the former, preliminary complexation of the magnesium reagent with the resident alkoxide, followed by alkyl group transfer, results in the exclusive formation of the syn product. Conversely, cuprate conjugate additions proceed in an anti fashion, presumably because, in this mode of addition, coulombic repulsions are minimized.

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