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Gold( I )‐Catalyzed 5‐ endo ‐ dig Carbocyclization of Acetylenic Dicarbonyl Compounds
Author(s) -
Staben Steven T.,
KennedySmith Joshua J.,
Toste F. Dean
Publication year - 2004
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.200460844
Subject(s) - dig , catalysis , iodide , chemistry , bicyclic molecule , diene , organic chemistry , combinatorial chemistry , medicinal chemistry , computer science , world wide web , natural rubber
Cyclopentenoid structures including compounds containing vinyl iodide, 1,3‐diene, and heterocyclic moieties are obtained through the gold( I )‐catalyzed 5‐ endo‐dig addition of β‐dicarbonyl compounds to unactivated alkynes under neutral conditions and at room temperature (RT). Both monocyclic and bicyclic cyclopentenes can be formed in excellent yields and with good diastereoselectivity (see scheme).