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Scalable Synthesis of Oxazolones from Propargylic Alcohols through Multistep Palladium(II) Catalysis: β‐Selective Oxidative Heck Coupling of Cyclic Sulfonyl Enamides and Aryl Boroxines
Author(s) -
Alamsetti Santosh Kumar,
Persson Andreas K. Å.,
Jiang Tuo,
Bäckvall JanE.
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.201307471
Subject(s) - catalysis , palladium , chemistry , aryl , combinatorial chemistry , reagent , organic chemistry , phenylacetic acid , scalability , computer science , database , alkyl
A whale of a scale : The title oxidative Heck coupling proceeded with unusual β selectivity to generate a variety of branched substituted oxazolones (see scheme; Ts= p ‐toluenesulfonyl). The three‐step synthesis from readily available starting materials with a simple palladium catalyst and inexpensive reagents could be carried out in a single reaction vessel or scaled up for the preparation of large amounts of these amino acid precursors.