TY - JOUR
T1 - Formal [3+2] Cycloaddition of Nitrosoallenes with Carbonyl and Nitrile Compounds to Form Functional Cyclic Nitrones
AU - Tanimoto, Hiroki
AU - Shitaoka, Takashi
AU - Yokoyama, Keiichi
AU - Morimoto, Tsumoru
AU - Nishiyama, Yasuhiro
AU - Kakiuchi, Kiyomi
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/10/7
Y1 - 2016/10/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84990853784&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.6b00758
DO - 10.1021/acs.joc.6b00758
M3 - 学術論文
C2 - 27225030
AN - SCOPUS:84990853784
SN - 0022-3263
VL - 81
SP - 8722
EP - 8735
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -