title: Single-Flask Multicomponent Synthesis of Highly Substituted α-Pyrones via a Sequential Enolate Arylation and Alkenylation Strategy.
abstract: Trisubstituted α-pyrones are obtained by a Pd-catalyzed three-component, single-flask operation via an α-arylation, subsequent α-alkenylation, alkene isomerization, and dienolate lactonization. A variety of coupling components under mild conditions afforded isolated yields of up to 93% of the pyrones with complete control of regioselectivity. Metal dependence was noted for three of the steps of the pathway. Utility of the pyrone products was demonstrated by further transformations providing convenient access to polyaromatic compounds, exhibiting broad molecular diversity.
authors: Department of Chemistry and Biochemistry, University of Notre Dame , Notre Dame, Indiana 46566, United States.
authors: Michael
authors: M
authors: Grigalunas
authors: Department of Chemistry and Biochemistry, University of Notre Dame , Notre Dame, Indiana 46566, United States.|Lab of Computational Chemistry and Drug Design, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School , Shenzhen 518055, China.
authors: Olaf
authors: O
authors: Wiest
authors: Department of Chemistry and Biochemistry, University of Notre Dame , Notre Dame, Indiana 46566, United States.
authors: Paul
authors: P
authors: Helquist
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D007659:Ketones; D011753:Pyrones; D010165:Palladium