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On the Structure of Intermediates in Enyne Gold(I)‐Catalyzed Cyclizations: Formation of trans ‐Fused Bicyclo[5.1.0]octanes as a Case Study
Author(s) -
Escofet Imma,
ArmengolRelats Helena,
Bruss Hanna,
Besora Maria,
Echavarren Antonio M.
Publication year - 2020
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.202004237
Subject(s) - enyne , bicyclic molecule , chemistry , catalysis , carbene , stereochemistry , cascade , reaction intermediate , computational chemistry , organic chemistry , chromatography
The nature of cyclopropyl gold(I) carbene‐type intermediates has been reexamined as part of a mechanistic study on the formation of cis ‐ or trans ‐fused bicyclo[5.1.0]octanes in a gold(I)‐catalyzed cascade reaction. Benchmark of DFT methods together with QTAIM theory and NBO analysis confirms the formation of distinct intermediates with carbenic or carbocationic structures in the cycloisomerizations of enynes.