title: Regioselective and stereoselective cyclizations of cyclohexadienones tethered to active methylene groups.
abstract: The cyclization of 2,5-cyclohexadienones tethered to activated methylene groups was studied. The substitution around the cyclohexadienone ring serves to regioselectively direct these cyclizations based primarily on electronic effects. In the case of brominated substrates, these reactions proceed to give highly unusual electron-deficient tricyclic cyclopropanes. By using a Cinchona alkaloid-based phase-transfer catalyst, prochiral cyclohexadienones can be desymmetrized with moderate stereoselectivity.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.
authors.forename: Rodolfo
authors.initials: R
authors.lastname: Tello-Aburto
authors.forename: Kyle A
authors.initials: KA
authors.lastname: Kalstabakken
authors.forename: Kelly A
authors.initials: KA
authors.lastname: Volp
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Harned
mesh_terms: D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002929:Cinchona / Q000737:chemistry; D002930:Cinchona Alkaloids / Q000737:chemistry; D003500:Cyclization; D053138:Cyclohexenes / Q000032:analysis / Q000737:chemistry*; D003521:Cyclopropanes / Q000032:analysis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002930:Cinchona Alkaloids; D053138:Cyclohexenes; D003521:Cyclopropanes; C507608:cyclohexadienone