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Synthesis 1991; 1991(12): 1083-1089
DOI: 10.1055/s-1991-28396
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On the Stereochemical Divergence in the Conjugate Addition of Lithium Dimethylcuprate/Trimethylsilyl Chloride to γ-Alkoxy and γ-Ureido α,β-Unsaturated Esters

Stephen Hanessian* , Kenzo Sumi
  • *Department of Chemistry, Université de Montréal, C. P 6128, Succ. A, Montréal, Quebec, H3C 3J7 Canada
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Publication Date:
29 April 2002 (online)

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A comparative study was made of the reaction of chiral non-racemic γ-alkoxy and γ-ureido-α,β-unsaturated esters with lithium dimethylcuprate in the presence of trimethylsilyl chloride. The possible origins of the anti- and syn-additions respectively are discussed and rationalized.