文献类型：期刊文献

英文题名：Iron(III)-Catalyzed Cycloisomerizations of Acetal-Vinylidenecyclopropanes: An Efficient Synthetic Route to 1,2-Disubstituted Cyclobutenes

作者：Yang, Song[1,2];Yuan, Wei[3];Xu, Qin[1,2];Shi, Min[1,2,3]

机构：[1]E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China;[3]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

年份：2015

卷号：21

期号：45

起止页码：15964

外文期刊名：CHEMISTRY-A EUROPEAN JOURNAL

收录：;EI(收录号：20153901301520);WOS:【SCI-EXPANDED(收录号:WOS:000363890700016)，CCR-EXPANDED(收录号:WOS:000363890700016)】；

基金：We are grateful for financial support from the National Basic Research Program of China [(973)-2015CB856603] and the National Natural Science Foundation of China (20472096, 21372241, 21361140350, 20672127, 21421091, 21372250, 21121062, 21302203, 20732008, and 21572052) for financial support.

语种：英文

外文关键词：cycloisomerization; homogeneous catalysis; iron; ring expansion; small ring systems

摘要：A novel iron(III)-catalyzed intramolecular cycloisomerization of acetal-vinylidenecyclopropanes to afford a series of halogenated 1,2-disubstituted cyclobutenes tethered with a tetrahydropyrrole has been developed. The reaction is thought to proceed through a formal iron-catalyzed Prins cyclization followed by a ring-enlarging rearrangement of the methylenecyclopropane carbocation. The present protocol provides an alternative route to functionalized disubstituted cyclobutenes and the corresponding products could be successfully transformed into eight-membered oxacyclic products.