Triflic Acid-Catalyzed Highly Stereoselective Friedel- Crafts Aminoalkylation of Indoles and Pyrroles

Abid Shaikh, Liliana Teixeira, Béla Török

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81 Scopus citations

Abstract

A simple and efficient synthesis to both enantiomers of highly enantiomerically enriched α-trifluoromethyl-α-(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-α-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.
Original languageAmerican English
JournalOrganic Letters
Volume10
StatePublished - 2008

Keywords

  • Stereoselective aminoalkylation
  • Triflic acid-catalyzed reaction

DC Disciplines

  • Chemistry

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