Journal
TETRAHEDRON
Volume 67, Issue 24, Pages 4442-4448Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.02.066
Keywords
Hetero-Diels-Alder cycloaddition; Photocatalysis; Radical anion
Categories
Funding
- ACS [49817-ND1]
- NIH [GM095666, RR08389-01]
- Sloan Foundation
- Beckman Foundation
- Research Corporation
- NSF [CHE-9208463, CHE-9629688]
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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. (C) 2011 Elsevier Ltd. All rights reserved.
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