Enantioselective Cyclopropanation of Allylic Alcohols. The Effect of Zinc Iodide

Scott E. Denmark, Stephen P. O'Connor

Research output: Contribution to journalArticlepeer-review

Abstract

The effect of zinc iodide on the catalytic, enantioselective cyclopropanation of aliylic alcohols is examined with bis(iodomethyl)zinc as the reagent and bis-methanesulfonamide 7 as the catalyst. Significant rate enhancement was observed when 1 equiv of zinc iodide was present, but more importantly, the enantiomeric excess of the product cyclopropane increased from 80% to 89% for the substrate cinnamyl alcohol. Reaction studies and spectroscopic investigations show that this remarkable influence is the result of reagent modification via a Schlenk equilibrium that produces the more reactive and selective species (iodomethyl)zinc iodide.

Original languageEnglish (US)
Pages (from-to)3375-3389
Number of pages15
JournalJournal of Organic Chemistry
Volume62
Issue number10
DOIs
StatePublished - 1997

ASJC Scopus subject areas

  • Organic Chemistry

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