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Pyrones as Substrates for Palladium–Catalyzed [4 + 3] Cycloadditions
Author(s) -
Trost Barry M.,
Schneider Stephan
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198902131
Subject(s) - cycloaddition , palladium , reagent , catalysis , chemistry , ring (chemistry) , combinatorial chemistry , reaction mechanism , medicinal chemistry , computational chemistry , organic chemistry
A novel reaction of pyrones was observed upon treatment with the palladium complex 1 , a 4π‐electron reagent. Whereas pyrones normally behave as 2π‐electron substrates toward 4π‐electron systems, they undergo [4 + 3] cycloaddition with 1 to give seven‐membered ring compounds such as 2 and 3 . A two‐step mechanism for the cycloaddition is offered as an explanation for this behavior.