Silver(I)-Catalyzed Stereochemical Isomerization of Cyclopropanols

Abstract

Isomerization of cyclopropane-containing molecules offers a direct pathway to access all of their diastereoisomers. Current catalytic methods, however, are largely confined to isomerization of carbonyl- and vinyl-substituted cyclopropanes. We report a catalytic isomerization of cyclopropanols, which converts readily accessible cis-1,2-disubstituted cyclopropanols into their more stable, yet often less accessible, trans-isomers. This enables a straightforward access to both diastereoisomers of these small-ring molecules. Mechanistic studies indicate the catalytic reactivity of silver homoenolates.