Iron(III)‐Catalyzed Cycloisomerizations of Acetal–Vinylidenecyclopropanes: An Efficient Synthetic Route to 1,2‐Disubstituted Cyclobutenes |
| |
| Authors: | Song Yang Wei Yuan Dr. Qin Xu Prof. Dr. Min Shi |
| |
| Affiliation: | 1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237 (P. R. China);2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032 (P. R. China). |
| |
| Abstract: | 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. |
| |
| Keywords: | cycloisomerization homogeneous catalysis iron ring expansion small ring systems |
|
|
