Chiral Amino Alcohol Modified Halomethylzinc Reagents

Scott E Denmark, James P. Edwards

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish (US)
Pages (from-to)229-230
Number of pages2
JournalSynlett
Volume1992
Issue number3
DOIs
StatePublished - Jan 1 1992

ASJC Scopus subject areas

  • Organic Chemistry

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