Scalable Synthesis of Oxazolones from Propargylic Alcohols through Multistep Palladium(II) Catalysis: β‐Selective Oxidative Heck Coupling of Cyclic Sulfonyl Enamides and Aryl Boroxines1. Issue 51 (31st October 2013)

• Record Type: Journal Article
• Authors: Alamsetti, Santosh Kumar; Persson, Andreas K. Å.; Jiang, Tuo; Bäckvall, Jan‐E.
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 51(2013)
• Page Start: 13745
• Page End: 13750
• Publication Date: 2013-10-31
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201307471
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>A whale of a scale</bold>: The title oxidative Heck coupling proceeded with unusual β selectivity to generate a variety of branched substituted oxazolones (see scheme; Ts=<italic>p</italic>‐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.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4t3jdzds" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>