title: Chiral polycyclic ketones via desymmetrization of dihaloolefins.
abstract: 3-Chloronorbornenone (R)-1a (98% ee) was obtained from trichloronorbornene 5 in two steps by the in situ generation of dichloronorbornadiene 2a with t-BuOK and desymmetrization with (-)-ephedrine, followed by hydrolysis with PPTS. The generality of this desymmetrization with (-)-ephedrine was tested with dibromonorbornadiene 2c and other substituted dichloronorbornadienes.
authors.affiliation: Dipartimento di Scienze Ambientali and Dipartimento di Chimica, Università Ca' Foscari di Venezia, Dorsoduro 2137, I-30123 Venezia, Italy. gborsato@unive.it
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Borsato
authors.forename: Anthony
authors.initials: A
authors.lastname: Linden
authors.forename: Ottorino De
authors.initials: OD
authors.lastname: Lucchi
authors.forename: Vittorio
authors.initials: V
authors.lastname: Lucchini
authors.forename: David
authors.initials: D
authors.lastname: Wolstenholme
authors.forename: Alfonso
authors.initials: A
authors.lastname: Zambon
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D004809:Ephedrine / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D006868:Hydrolysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009636:Norbornanes / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D006219:Halogens; D007659:Ketones; D009636:Norbornanes; D011083:Polycyclic Compounds; D004809:Ephedrine