Catalytic enantioselective cyclopropanation with bis(halomethyl)zinc reagents. I. Optimization of reaction protocol

Scott E. Denmark, Beritte L. Christenson, Diane M. Coe, Stephen P. O'Connor

Research output: Contribution to journalArticle


The rate and selectivity of catalytic enantioselective cyclopropanation of cinnamyl alcohol utilizing bisiodomethyl zinc and 4a/4b is greatly dependent on the order of addition of the reagents. The independent preformation of the ethylzinc cinnamyloxide and bis(iodomethyl)zinc was found to be crucial. The reaction displayed autocatalytic behavior which was shown to be due to the generation of zinc iodide.

Original languageEnglish (US)
Pages (from-to)2215-2218
Number of pages4
JournalTetrahedron Letters
Issue number13
StatePublished - Mar 27 1995



  • Allylic alcohol
  • bis(iodomethyl)zinc
  • cyclopropanation
  • diethylzinc

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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