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Rhodium(I)‐Catalyzed [4+1] Cycloaddition Reactions of α,β‐Unsaturated Imines with Terminal Alkynes for the Preparation of Pyrrole Derivatives
Author(s) -
Mizuno Akio,
Kusama Hiroyuki,
Iwasawa Nobuharu
Publication year - 2009
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.200904402
Subject(s) - rhodium , pyrrole , chemistry , cyclooctene , catalysis , cycloaddition , imine , intramolecular force , medicinal chemistry , nucleophile , nitrogen atom , polymer chemistry , organic chemistry , ring (chemistry)
Rhodium vinylidene intermediates are characteristic for the title reaction (see scheme; coe=cyclooctene, cy=cyclohexyl). This reaction proceeds by the nucleophilic addition of the nitrogen atom of the imine to the rhodium vinylidene complex to give a zwitterionic intermediate, which undergoes intramolecular cyclization to afford the corresponding pyrrole.