Formal [3+2] Cycloaddition of Nitrosoallenes with Carbonyl and Nitrile Compounds to Form Functional Cyclic Nitrones

Hiroki Tanimoto*, Takashi Shitaoka, Keiichi Yokoyama, Tsumoru Morimoto, Yasuhiro Nishiyama, Kiyomi Kakiuchi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

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.

Original languageEnglish
Pages (from-to)8722-8735
Number of pages14
JournalJournal of Organic Chemistry
Volume81
Issue number19
DOIs
StatePublished - 2016/10/07

ASJC Scopus subject areas

  • Organic Chemistry

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