Brønsted acid catalyzed enantioselective indole aza-Claisen rearrangement mediated by an arene CH-O interaction

Pradip Maity, Ryan P. Pemberton, Dean J. Tantillo, Uttam K. Tambar

Research output: Contribution to journalArticle

48 Citations (Scopus)

Abstract

Although the aromatic aza-Claisen rearrangement is a general strategy for accessing substituted aromatic amines, there are no highly enantioselective examples of this process. We report the first Brønsted acid catalyzed enantioselective indole aza-Claisen rearrangement for the synthesis of chiral 3-amino-2-substituted indoles. We present evidence for an arene CH-O interaction as a source of activation and stereoinduction, which is an unprecedented phenomenon in enantioselective Brønsted acid catalysis. The products of this reaction can be transformed into 3-aminooxindoles, which are prevalent in many biologically active small molecules.

Original languageEnglish (US)
Pages (from-to)16380-16383
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number44
DOIs
StatePublished - Nov 6 2013

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Indoles
Acids
Catalysis
Amines
Chemical activation
Molecules
indole

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Brønsted acid catalyzed enantioselective indole aza-Claisen rearrangement mediated by an arene CH-O interaction. / Maity, Pradip; Pemberton, Ryan P.; Tantillo, Dean J.; Tambar, Uttam K.

In: Journal of the American Chemical Society, Vol. 135, No. 44, 06.11.2013, p. 16380-16383.

Research output: Contribution to journalArticle

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