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Enantioselective Cyclopropanation of Allylic Alcohols. The Effect of Zinc Iodide. | LitMetric

Enantioselective Cyclopropanation of Allylic Alcohols. The Effect of Zinc Iodide.

J Org Chem

Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801.

Published: May 1997

AI Article Synopsis

Article Abstract

The effect of zinc iodide on the catalytic, enantioselective cyclopropanation of allylic 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.

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http://dx.doi.org/10.1021/jo9702397DOI Listing

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