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.
Org Lett. 2016 Nov 4;18(21):5724-5727. doi: 10.1021/acs.orglett.6b02969. Epub 2016 Oct 21.
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.
三取代的α-吡喃酮可以通过 Pd 催化的三组分、单瓶操作，经过α-芳基化、随后的α-烯基化、烯烃异构化和烯醇化物内酯化反应得到。在温和条件下，各种偶联组件可以提供高达 93%的孤立收率的吡喃酮，并且对区域选择性具有完全的控制。该途径的三个步骤中注意到了金属依赖性。吡喃酮产物的用途通过进一步的转化得到了证明，为多环芳烃化合物的提供了便利的合成途径，展示了广泛的分子多样性。
