Chiral Brønsted acid catalyzed stereoselective addition of azlactones to 3-vinylindoles for facile access to enantioenriched tryptophan derivatives

Masahiro Terada, Kenichi Moriya, Kyohei Kanomata, Keiichi Sorimachi

Research output: Contribution to journalArticlepeer-review

72 Citations (Scopus)

Abstract

Syn-gled out: The syn diastereo- and enantioselective addition of azlactones to 3-vinylindoles was accomplished by using a chiral, binapthol-derived, Brønsted acid catalyst (see scheme). This method enables facile access to tryptophan derivatives with adjacent quaternary and tertiary stereogenic centers, which are potentially useful for the synthesis of peptidomimetics.

Original languageEnglish
Pages (from-to)12586-12590
Number of pages5
JournalAngewandte Chemie - International Edition
Volume50
Issue number52
DOIs
Publication statusPublished - 2011 Dec 23

Keywords

  • asymmetric catalysis
  • azlactones
  • indoles
  • organocatalysis
  • tryptophan

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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