title: Phosphine-Catalyzed Intramolecular Cyclizations of α-Nitroethylallenoates Forming (Z)-Furanone Oximes.
abstract: A novel and efficient phosphine-catalyzed intramolecular cyclization of α-nitroethylallenic esters is reported. This process appears to be practical for the stereoselective syntheses of (Z)-furan-2(3H)-one oxime derivatives in excellent yields. Mechanistically, the reaction involves a phosphine-catalyzed Michael addition of an alkylideneazinate and rearrangement of the cyclic nitronate to the α-nitrosodihydrofuran.
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University , Nanjing, 210009, P. R. China.|Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
authors.forename: Qing-Fa
authors.initials: QF
authors.lastname: Zhou
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
authors.forename: Kui
authors.initials: K
authors.lastname: Zhang
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
authors.forename: Lingchao
authors.initials: L
authors.lastname: Cai
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
authors.forename: Ohyun
authors.initials: O
authors.lastname: Kwon
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D009574:Nitro Compounds / Q000737:chemistry*; D010091:Oximes / Q000138:chemical synthesis*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D005663:Furans; D009574:Nitro Compounds; D010091:Oximes; D010720:Phosphines; C025947:propadiene