Abstract
Densely substituted cyclopropanol and cyclopropylazole derivatives with three stereogenic carbons in the small cycle are obtained via a highly diastereoselective formal nucleophilic substitution of bromocyclopropanes. The chiral center at C-2 in bromocyclopropane dictates the configuration of the other two stereocenters that are successively installed via a sterically controlled addition of a nucleophile, followed by a thermodynamically driven epimerization of the resulting enolate intermediate.
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