Regio‐ and Diastereoselective CC Coupling of α‐Olefins and Styrenes to 3‐Hydroxy‐2‐oxindoles by Ru‐Catalyzed Hydrohydroxyalkylation | Zendy

Yamaguchi Eiji | Zendy; Mowat Jeffrey | Zendy; Luong Tom | Zendy; Krische Michael J. | Zendy

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Regio‐ and Diastereoselective CC 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.

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