Literature DB >> 18254637

Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles.

Mohammed Abid1, Liliana Teixeira, Béla Török.   

Abstract

A simple and efficient synthesis to both enantiomers of highly enantiomerically enriched alpha-trifluoromethyl-alpha-(heteroaryl)-glycine derivatives via highly stereoselective aminoalkylation of indoles and pyrroles is described. The triflic acid-catalyzed reaction of enantiomeric 3,3,3-trifluoro-pyruvate-alpha-methylbenzyl imines with indoles and pyrroles and the subsequent Pd-catalyzed hydrogenolysis of the methylbenzyl group provided the products in high yields and excellent enantioselectivities.

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Year:  2008        PMID: 18254637     DOI: 10.1021/ol703095d

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


  5 in total

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Authors:  Guangkuan Zhao; Shyam S Samanta; Jessica Michieletto; Stéphane P Roche
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Journal:  ChemMedChem       Date:  2012-02-20       Impact factor: 3.466

4.  Ethyl 3,3,3-trifluoro-2-hy-droxy-2-(5-meth-oxy-1H-indol-3-yl)propionate.

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5.  Chiral Brønsted acid-catalyzed enantioselective Friedel-Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ.

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Journal:  Chem Sci       Date:  2015-10-30       Impact factor: 9.825

  5 in total

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