Enantioselective Friedel-Crafts alkylation of 4,7-dihydroindoles with enones catalyzed by primary-secondary diamines

Liang Hong, Wangsheng Sun, Chunxia Liu, Lei Wang, Kwok Yin Wong, Rui Wang

Research output: Journal article publicationJournal articleAcademic researchpeer-review

66 Citations (Scopus)

Abstract

A study was conducted to demonstrate the development of a new chiral primary-secondary diamine catalyst derived from amino acid and its application in the asymmetric Friedel-Crafts alkylation of 4,7-dihydroindoles with α-βunsaturated enones. A array of primary amines derived from amino acids were investigated in the asymmetric Friedel-Crafts alkylation of 4,7-dihydroindole with benzylideneacetone in toluene. It was found that the length of the alkyl chain influenced the catalytic activity of the primary amine catalyst and the n-propylated catalyst gave the best result. It was also observed that the acid co-catalyst had a great impact on the reaction. The scope and limitations of the method was examined with regard to the enone and 4,7-dihydroindole substrates after establishing optimal reaction conditions.
Original languageEnglish
Pages (from-to)11105-11108
Number of pages4
JournalChemistry - A European Journal
Volume15
Issue number42
DOIs
Publication statusPublished - 26 Oct 2009

Keywords

  • Conjugate addition
  • Enantioselectivity
  • Enones
  • Friedel-crafts reaction
  • Organocatalysis

ASJC Scopus subject areas

  • Chemistry(all)

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