Literature DB >> 19603799

A novel Prins cyclization through benzylic/allylic C-H activation.

Binxun Yu1, Tuo Jiang, Junpeng Li, Yingpeng Su, Xinfu Pan, Xuegong She.   

Abstract

A step-economic method to construct the tetrahydropyran ring, involving sequential benzylic/allylic C-H bond activation via DDQ oxidation and nucleophilic attack of an unactivated olefin, is described. The equatorial-trisubstituted Prins products are obtained from benzyl and allyl homoallylic ethers with high yield and stereochemical fidelity.

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Year:  2009        PMID： 19603799     DOI： 10.1021/ol901291w

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Synthesis of Functionalized 4-Methylenetetrahydropyrans by Oxidative Activation of Cinnamyl or Benzyl Ethers.

Authors:  Arun K Ghosh; Xu Cheng
Journal:  Tetrahedron Lett       Date:  2012-05-16       Impact factor: 2.415

2.  Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent.

Authors:  Arun K Ghosh; Xu Cheng
Journal:  Org Lett       Date:  2011-07-12       Impact factor: 6.005

3.  2,3-Dichloro-5,6-dicyano-1,4-benzoquinone-catalyzed reactions employing MnO2 as a stoichiometric oxidant.

Authors:  Lei Liu; Paul E Floreancig
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

4.  Aromatic cations from oxidative carbon-hydrogen bond cleavage in bimolecular carbon-carbon bond forming reactions.

Authors:  Dane J Clausen; Paul E Floreancig
Journal:  J Org Chem       Date:  2012-07-16       Impact factor: 4.354

5.  Total Synthesis of Potent Antitumor Macrolide, (-)-Zampanolide: An Oxidative Intramolecular Cyclization-Based Strategy.

Authors:  Arun K Ghosh; Xu Cheng; Ruoli Bai; Ernest Hamel
Journal:  European J Org Chem       Date:  2012-07-01

Review 6.  Quinone-Catalyzed Selective Oxidation of Organic Molecules.

Authors:  Alison E Wendlandt; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-04       Impact factor: 15.336

7.  Efficient, highly diastereoselective MS 4 Å-promoted one-pot, three-component synthesis of 2,6-disubstituted-4-tosyloxytetrahydropyrans via Prins cyclization.

Authors:  Naseem Ahmed; Naveen Kumar Konduru
Journal:  Beilstein J Org Chem       Date:  2012-02-01       Impact factor: 2.883

8.  Tandem C-H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (-)-brussonol and (-)-przewalskine E.

Authors:  Zhi-Wei Jiao; Yong-Qiang Tu; Qing Zhang; Wen-Xing Liu; Shu-Yu Zhang; Shao-Hua Wang; Fu-Min Zhang; Sen Jiang
Journal:  Nat Commun       Date:  2015-06-17       Impact factor: 14.919
  8 in total

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