Enantioselective organocatalytic synthesis of quaternary α-amino acids bearing a CF3 Moiety

Ralph Husmann, Erli Sugiono, Stefanie Mersmann, Gerhard Raabe, Magnus Rueping, Carsten Bolm*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

104 Scopus citations

Abstract

A highly enantioselective Friedel-Crafts reaction catalyzed by a chiral phosphoric acid was developed. N-Boc-protected ethyl trifluoropyruvate imine was activated by 6 mol % of catalyst and reacted with a wide variety of indole derivatives to afford quaternary α-amino acids in excellent yields (up to 99%) and high enantioselectivities (up to 98:2 er).(Figure Presented)

Original languageEnglish (US)
Pages (from-to)1044-1047
Number of pages4
JournalOrganic Letters
Volume13
Issue number5
DOIs
StatePublished - Mar 4 2011

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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