Literature DB >> 20187623

Cationic gold(I)-catalyzed intramolecular cyclization of gamma-hydroxyalkynones into 3(2H)-furanones.

Masahiro Egi1, Kenji Azechi, Moriaki Saneto, Kaori Shimizu, Shuji Akai.   

Abstract

The combination of (p-CF(3)C(6)H(4))(3)PAuCl and AgOTf generates a powerful catalyst for the intramolecular cyclizations of readily available gamma-hydroxyalkynones under mild conditions. The substituted 3(2H)-furanones are obtained in 55-94% yields. This method is also applicable to the preparation of 2,3-dihydro-4H-pyran-4-ones.

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Year:  2010        PMID: 20187623     DOI: 10.1021/jo100048j

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

1.  Synthesis of oxazocenones via gold(I)-catalyzed 8-endo-dig hydroalkoxylation of alkynamides.

Authors:  Stephen S Scully; Shao-Liang Zheng; Bridget K Wagner; Stuart L Schreiber
Journal:  Org Lett       Date:  2015-01-08       Impact factor: 6.005

2.  Enantioselective synthesis of 3,4-dihydro-1,2-oxazepin-5(2H)-ones and 2,3-dihydropyridin-4(1H)-ones from β-substituted β-hydroxyaminoaldehydes.

Authors:  Adwait R Ranade; Gunda I Georg
Journal:  J Org Chem       Date:  2014-01-13       Impact factor: 4.354

3.  Highly efficient mesoporous polymer supported phosphine-gold(i) complex catalysts for amination of allylic alcohols and intramolecular cyclization reactions.

Authors:  Huoliang Gu; Xiong Sun; Yong Wang; Haihong Wu; Peng Wu
Journal:  RSC Adv       Date:  2018-01-08       Impact factor: 4.036

4.  Gold(I)-catalyzed formation of furans from γ-acyloxyalkynyl ketones.

Authors:  Marie Hoffmann; Solène Miaskiewicz; Jean-Marc Weibel; Patrick Pale; Aurélien Blanc
Journal:  Beilstein J Org Chem       Date:  2013-08-30       Impact factor: 2.883

5.  A tandem Mannich addition-palladium catalyzed ring-closing route toward 4-substituted-3(2H)-furanones.

Authors:  Jubi John; Eliza Târcoveanu; Peter G Jones; Henning Hopf
Journal:  Beilstein J Org Chem       Date:  2014-06-27       Impact factor: 2.883

  5 in total

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