189632-07-3Relevant academic research and scientific papers
Enantioselective Cyclopropanation of Allylic Alcohols. The Effect of Zinc Iodide
Denmark, Scott E.,O'Connor, Stephen P.
, p. 3375 - 3389 (1997)
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.
