4.6 Article

Organic Photocatalytic Cyclization of Polyenes: A Visible-Light-Mediated Radical Cascade Approach

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 42, Pages 14723-14727

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201503118

Keywords

cyclization; organocatalysis; photocatalysis; polyenes; radical reactions

Funding

  1. Ministry of Science and Technology [2012CB821600]
  2. Natural Science Foundation of China (NSFC) [21390400, 21202171, 21025208]
  3. Chinese Academy of Sciences
  4. National Program for Support of Top-Notch Young Professionals

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A visible-light-mediated, organic photocatalytic stereoselective radical cascade cyclization of polyprenoids is described. The desired cascade cyclization products are achieved in good yields and high stereoselectivities with eosin Y as photocatalyst in hexafluoro-2-propanol. The catalyst system is also suitable for 1,3-dicarbonyl compounds, which require only catalytic amounts of LiBr to promote the formation of the corresponding enols.

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