title: Halocycloalkenones as Diels-Alder dienophiles. Applications to generating useful structural patterns.
abstract: Halocycloalkenones are demonstrated to function as potent dienophiles in inter- and intramolecular Diels-Alder cycloadditions. We have found 2-brominated cycloalkenone dienophiles to be both highly endo selective and significantly more reactive than their nonhalogenated parent compounds. A method for the facile conversion of brominated cyclobutanone DA adducts to synthetically useful cyclopropyl functional handles is described.
authors.affiliation: Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, United States.
authors.forename: Audrey G
authors.initials: AG
authors.lastname: Ross
authors.forename: Steven D
authors.initials: SD
authors.lastname: Townsend
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Danishefsky
mesh_terms: D003500:Cyclization; D003516:Cycloparaffins / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003516:Cycloparaffins; D006846:Hydrocarbons, Halogenated