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Iron(III)‐Catalyzed Cycloisomerizations of Acetal–Vinylidenecyclopropanes: An Efficient Synthetic Route to 1,2‐Disubstituted Cyclobutenes
Author(s) -
Yang Song,
Yuan Wei,
Xu Qin,
Shi Min
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502634
Subject(s) - cycloisomerization , acetal , chemistry , intramolecular force , catalysis , carbocation , ring (chemistry) , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry
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.