title: A Torquoselective Extrusion of Isoxazoline N-Oxides. Application to the Synthesis of Aryl Vinyl and Divinyl Ketones for Nazarov Cyclization.
abstract: A mild, convenient reaction sequence for the synthesis of Nazarov cyclization substrates is described. The [3+2] dipolar cycloaddition of a nitrone and an electron-deficient alkyne gives an isolable isoxazoline intermediate, which upon oxidation undergoes stereoselective extrusion of nitrosomethane to give aryl vinyl or divinyl ketones.
authors.affiliation: Department of Chemistry, University of Rochester, Rochester, New York, 14627.
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Canterbury
authors.forename: Ildiko R
authors.initials: IR
authors.lastname: Herrick
authors.forename: Joann
authors.initials: J
authors.lastname: Um
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
authors.forename: Alison J
authors.initials: AJ
authors.lastname: Frontier