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Palladium‐Catalyzed Cascade to Benzoxepins by Using Vinyl‐Substituted Donor–Acceptor Cyclopropanes
Author(s) -
Faltracco Matteo,
Vrande Koen N. A.,
Dijkstra Martijn,
Saya Jordy M.,
Hamlin Trevor A.,
Ruijter Eelco
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202102862
Subject(s) - cyclopropane , palladium , chemistry , moiety , phosphonate , catalysis , acceptor , ligand (biochemistry) , yield (engineering) , intermolecular force , combinatorial chemistry , cascade , organic chemistry , molecule , ring (chemistry) , materials science , biochemistry , physics , receptor , chromatography , metallurgy , condensed matter physics
A palladium‐catalyzed intermolecular cascade (4+3) cyclocondensation of salicylaldehydes and vinylcyclopropanes is reported. A key feature of the reaction is the use of a phosphonate group as an acceptor moiety on the cyclopropane, exploiting its propensity to undergo olefination with aldehydes. Subsequent O‐allylation enabled the formation of a range of substituted benzoxepinsWith a novel chiral ligand, the products were obtained in generally good yield and with reasonable enantioselectivity.