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Chemistry. 2015 Oct 12;21(42):14723-7. doi: 10.1002/chem.201503118. Epub 2015 Sep 01.

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

Chemistry (Weinheim an der Bergstrasse, Germany)

Zhongbo Yang, Han Li, Long Zhang, Ming-Tian Zhang, Jin-Pei Cheng, Sanzhong Luo

Affiliations

  1. Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449http://luosz.iccas.ac.cn.
  2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071 (China).
  3. Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China).
  4. Center of Basic Molecular Science (CBMS) Department of Chemistry, Tsinghua University, Beijing, 100084 (China). [email protected].
  5. Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100190 (China), Fax: (+86)-10-6255-4449http://luosz.iccas.ac.cn. [email protected].
  6. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071 (China). [email protected].

PMID: 26332702 DOI: 10.1002/chem.201503118

Abstract

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.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: cyclization; organocatalysis; photocatalysis; polyenes; radical reactions

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