Literature DB >> 19518152

Lewis acid-catalyzed diastereoselective hydroarylation of benzylidene malonic esters.

Shaofeng Duan1, Ranjan Jana, Jon A Tunge.   

Abstract

Herein we report that simple Lewis acids catalyze the hydroarylation of benzylidene malonates with phenols. Ultimately, 3,4-disubstituted dihydrocoumarins are obtained via a hydroarylation-lactonization sequence. Moreover, the dihydrocoumarins are formed with a high degree of diastereoselectivity favoring the trans stereoisomer.

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Year:  2009        PMID： 19518152      PMCID： PMC2882201          DOI： 10.1021/jo900367g

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


  9 in total

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Journal:  Org Lett       Date:  2008-05-27       Impact factor: 6.005

4.  Trifluoroacetic acid-mediated hydroarylation: synthesis of dihydrocoumarins and dihydroquinolones.

Authors:  Kelin Li; Lindsay N Foresee; Jon A Tunge
Journal:  J Org Chem       Date:  2005-04-01       Impact factor: 4.354

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6.  AlCl3-mediated direct carbon-carbon bond-forming reaction of alpha-hydroxyketene-S,S-acetals with arenes and synthesis of 3,4-disubstituted dihydrocoumarin derivatives.

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Journal:  J Org Chem       Date:  2008-02-22       Impact factor: 4.354

7.  Chemical libraries via sequential C-H functionalization of phenols.

Authors:  Kelin Li; Jon A Tunge
Journal:  J Comb Chem       Date:  2008-01-31

8.  Enantioselective Friedel-Crafts reaction of indoles with arylidene malonates catalyzed by iPr-bisoxazoline-Cu(OTf)2.

Authors:  Jian Zhou; Yong Tang
Journal:  Chem Commun (Camb)       Date:  2004-01-19       Impact factor: 6.222

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Journal:  Bioorg Med Chem Lett       Date:  2007-06-20       Impact factor: 2.823
  9 in total
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1.  Mechanistic origin of the stereodivergence in decarboxylative allylation.

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  1 in total

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