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Cyclopentene Synthesis by a Catalytic [3+2] Annulation of Donor‐Acceptor Cyclopropanes with Polarized Alkenes
Author(s) -
Xu Cong,
Wei Na,
Zhu Dongsheng,
Wang Mang
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002967
Subject(s) - annulation , cyclopentene , chemistry , catalysis , ketene , intramolecular force , lewis acids and bases , acceptor , medicinal chemistry , ring (chemistry) , photochemistry , stereochemistry , organic chemistry , physics , condensed matter physics
[3+2] Annulation of donor‐acceptor cyclopropanes with alkynes represents an efficient route to cyclopentenes. Here, we describe a new cyclopentene synthesis via Lewis acid‐catalyzed ring‐opening addition and intramolecular S N V reaction of donor‐acceptor cyclopropanes with alkenes. The reaction is carried out under the catalysis of Sc(OTf) 3 by using polarized alkenes, namely α‐oxo ketene dithioacetals, as 2 C partners.