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Alkene‐Directed N ‐Attack Chemoselectivity in the Gold‐Catalyzed [2+2+1]‐Annulations of 1,6‐Enynes with N ‐Hydroxyanilines
Author(s) -
Huple Deepak B.,
Mokar Bhanudas D.,
Liu RaiShung
Publication year - 2015
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.201507946
Subject(s) - chemoselectivity , alkene , catalysis , chemistry , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry
Kinetically unstable nitrones are generated from gold‐catalyzed reactions of 1,6‐enynes with N ‐hydroxyanilines, and subsequently trapped by tethered alkenes to furnish [2+2+1]‐annulations. Our experimental data reveal that such nitrones arise from atypical N ‐attack chemoselectivity that is triggered by tethered alkenes to facilitate the key protodeauration reaction.