title: Formal [3+2] Cycloaddition of Nitrosoallenes with Carbonyl and Nitrile Compounds to Form Functional Cyclic Nitrones.
abstract: The synthesis of functional cyclic nitrones via [3+2] cycloadditions of allenamide-derived nitrosoallenes with carbonyl/nitrile compounds, including ketones, esters, and nitriles, is presented herein. Rapid carbon-carbon, carbon-oxygen, and carbon-nitrogen bond formations were achieved with in situ prepared nitrosoallenes, and densely substituted oxacyclic and carbocyclic nitrones containing tetrasubstituted carbon centers were successfully synthesized. The spirocyclic nitrone products synthesized from cyclic dicarbonyl compounds underwent the unique skeletal rearrangements to cyclic α-ketonitrones.
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST) , 8916-5 Takayamacho, Ikoma, Nara 630-0192, Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Tanimoto
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST) , 8916-5 Takayamacho, Ikoma, Nara 630-0192, Japan.
authors.forename: Takashi
authors.initials: T
authors.lastname: Shitaoka
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST) , 8916-5 Takayamacho, Ikoma, Nara 630-0192, Japan.
authors.forename: Keiichi
authors.initials: K
authors.lastname: Yokoyama
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST) , 8916-5 Takayamacho, Ikoma, Nara 630-0192, Japan.
authors.forename: Tsumoru
authors.initials: T
authors.lastname: Morimoto
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST) , 8916-5 Takayamacho, Ikoma, Nara 630-0192, Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Nishiyama
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST) , 8916-5 Takayamacho, Ikoma, Nara 630-0192, Japan.
authors.forename: Kiyomi
authors.initials: K
authors.lastname: Kakiuchi