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

Abid Shaikh, Liliana Teixeira, Béla Török

Research output: Contribution to journalArticlepeer-review

86 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 languageEnglish
Pages (from-to)933-935
Number of pages3
JournalOrganic Letters
Volume10
Issue number5
DOIs
StatePublished - Mar 6 2008

Scopus Subject Areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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