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Regio‐ and Diastereoselective CC Coupling of α‐Olefins and Styrenes to 3‐Hydroxy‐2‐oxindoles by Ru‐Catalyzed Hydrohydroxyalkylation
Author(s) -
Yamaguchi Eiji,
Mowat Jeffrey,
Luong Tom,
Krische Michael J.
Publication year - 2013
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.201303552
Subject(s) - catalysis , coupling (piping) , chemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , composite material
The direct approach : Ruthenium(0)‐catalyzed hydrohydroxyalkylation of α‐olefins and styrenes with 3‐hydroxy‐2‐oxindoles forms branched products of CC coupling with high levels of diastereocontrol. A mechanism involving diene–olefin oxidative coupling and a subsequent carboxylic acid co‐catalyzed transfer hydrogenolysis of the resulting oxaruthenacycle intermediate is postulated.