Visible Light Photocatalysis of Radical Anion Hetero-Diels-Alder Cycloadditions |
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Authors: | Hurtley Anna E Cismesia Megan A Ischay Michael A Yoon Tehshik P |
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Institution: | Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706, USA |
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Abstract: | We have discovered a photocatalytic intramolecular hetero-Diels-Alder reaction of tethered bis(enones). This transformation involves the intermediacy of an enone radical anion and constitutes the formal coupling of an electron-deficient heterodiene with an electronically mismatched enone dienophile. The diastereoselectivity and regioselectivity of the process are high, and the dihydropyran products are amenable to a variety of synthetically useful transformations. |
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Keywords: | Hetero-Diels-Alder cycloaddition Photocatalysis Radical anion |
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