Silver(I)-Catalyzed Stereochemical Isomerization of Cyclopropanols

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.