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Synlett 1992; 1992(3): 229-230
DOI: 10.1055/s-1992-21322
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Chiral Amino Alcohol Modified Halomethylzinc Reagents

Scott E. Denmark* , James P. Edwards
  • *Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA
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Publication Date:
08 March 2002 (online)

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The enantioselective cyclopropanation of cinnamyl alcohol (3) to 2-phenylcyclopropanemethanol (4) using (1R,2S)-N-methylephedrine-modified halomethylzinc reagents is reported. Modest (up to 24% ee) enantioselectivites were observed, and a solvent induced reversal of selectivity was noted. These studies demonstrated the potential for chiral zinc species to differentiate olefin enantiofaces in the delivery of methylene to prochiral allylic alcohols.