Title |
Formal [3+2] Cycloaddition of Nitrosoallenes with Carbonyl and Nitrile Compounds to Form Functional Cyclic Nitrones
|
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Published in |
Journal of Organic Chemistry, May 2016
|
DOI | 10.1021/acs.joc.6b00758 |
Pubmed ID | |
Authors |
Hiroki Tanimoto, Takashi Shitaoka, Keiichi Yokoyama, Tsumoru Morimoto, Yasuhiro Nishiyama, Kiyomi Kakiuchi |
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. |
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