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Gold‐Catalyzed [3+2] Cycloaddition/Hydrolytic Michael Addition/Retro‐Aldol Reactions of Propargylic Esters Tethered to Cyclohexadienones
Author(s) -
Cai Shunyou,
Liu Zheng,
Zhang Weibin,
Zhao Xinyang,
Wang David Zhigang
Publication year - 2011
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.201104028
Subject(s) - chemistry , cycloaddition , catalysis , aldol reaction , hydrolysis , michael reaction , stereochemistry , organic chemistry , medicinal chemistry
A golden dance! A series of symmetric and nonsymmetric propargylic esters tethered to cyclohexadienones were found to undergo the title reaction sequence under mild reaction conditions through gold catalysis. The product cyclohexenones or cyclohexanones having a γ‐quaternary center arise from simultaneous multiatom transpositions with complete stereochemical control.