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Synlett 1999; 1999(11): 1811-1813
DOI: 10.1055/s-1999-2931
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Catalytic Asymmetric Conjugate Addition on Macrocyclic and Acyclic Enones. Synthesis of R-(-)-Muscone

Alexandre Alexakis* , Cyril Benhaïm, Xavier Fournioux, Alexandra van den Heuvel, Jean-Marc Levêque, Sebastien March, Stephane Rosset
  • *Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, Genève 4, Switzerland CH-1211; Fax 41 22 3 28 73 96; E-mail: alexandre.alexakis@chiorg.unige.ch
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Publication Date:
31 December 1999 (online)

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The asymmetric conjugate addition of diethyl zinc to acyclic enones is described. With 1% Cu(OTf)2 and 2% of a chiral phosphite ligand, the catalyst allowed ee's up to 92'% to be obtained. The addition of dimethyl zinc to a macrocyclic 15-membered ring enone lead to optically active R-(-)-muscone, in 53% yield and 79% enantiomeric excess.

conjugate addition - catalysis - copper - asymmetry - dialkyl zinc - muscone