Visible Light Photocatalysis of Radical Anion Hetero-Diels-Alder Cycloadditions.

Autor: Hurtley AE; Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706., Cismesia MA, Ischay MA, Yoon TP
Jazyk: angličtina
Zdroj: Tetrahedron [Tetrahedron] 2011 Jun 17; Vol. 67 (24), pp. 4442-4448.
DOI: 10.1016/j.tet.2011.02.066
Abstrakt: 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.
Databáze: MEDLINE