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Visible‐Light‐Promoted Polycyclizations of Dienynes
Author(s) -
Lanzi Matteo,
Santacroce Veronica,
Balestri Davide,
Marchiò Luciano,
Bigi Franca,
Maggi Raimondo,
Malacria Max,
Maestri Giovanni
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201902837
Subject(s) - stereocenter , chemistry , intermolecular force , alkyne , bicyclic molecule , reactive intermediate , stereochemistry , bridging (networking) , molecule , catalysis , organic chemistry , enantioselective synthesis , computer network , computer science
A variety of linear dienynes can deliver complex tetracyclic frameworks in the presence of an Ir III complex and visible light. Product formation involves the generation of four new C−C bonds and six contiguous stereocenters, which decorate two [3.1.0] bicyclic units tethered through their bridging quaternary carbon atoms. The internal alkyne acts as a formal dicarbenoid for the generation of two cyclopropanes in these radical cation cascades. This behavior has not been previously observed for organic reactive intermediates and can be extended to intermolecular reactions and diendiynes.