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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201902837
Subject(s) - stereocenter , intermolecular force , chemistry , alkyne , bicyclic molecule , bridging (networking) , stereochemistry , reactive intermediate , photochemistry , molecule , catalysis , enantioselective synthesis , organic chemistry , computer science , computer network
Abstract 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.