title: Dual control of the selectivity in the formal nucleophilic substitution of bromocyclopropanes en route to densely functionalized, chirally rich cyclopropyl derivatives.
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.
authors.affiliation: Department of Chemistry, University of Kansas 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States, and Department of Chemistry, Missouri State University , 456 Temple Hall, Springfield, Missouri 65897, United States.
authors.forename: Pavel
authors.initials: P
authors.lastname: Ryabchuk
authors.forename: Andrew
authors.initials: A
authors.lastname: Edwards
authors.forename: Nikolay
authors.initials: N
authors.lastname: Gerasimchuk
authors.forename: Marina
authors.initials: M
authors.lastname: Rubina
authors.forename: Michael
authors.initials: M
authors.lastname: Rubin
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D003521:Cyclopropanes; D006842:Hydrocarbons, Brominated