title: Scalable synthesis of oxazolones from propargylic alcohols through multistep palladium(II) catalysis: β-selective oxidative Heck coupling of cyclic sulfonyl enamides and aryl boroxines.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm (Sweden).
authors.forename: Santosh Kumar
authors.initials: SK
authors.lastname: Alamsetti
authors.forename: Andreas K Å
authors.initials: AK
authors.lastname: Persson
authors.forename: Tuo
authors.initials: T
authors.lastname: Jiang
authors.forename: Jan-E
authors.initials: JE
authors.lastname: Bäckvall
keywords: arylation; boroxines; oxazolones; oxidative Heck coupling; palladium