Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization

Jonathan Clayden*, Christel J. Menet, Kirill Tchabanenko

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

73 Citations (Scopus)

Abstract

Chiral lithium amide bases are able to deprotonate N-benzyl-N-cumyl anisamides enantioselectively to yield enantiomerically enriched benzylic organolithiums. These spontaneously undergo dearomatising cyclisation to yield, in high enantiomeric excess enantiomerically enriched partially saturated isoindolones, which in some cases may be recrystallised to enantiomeric purity. These isoindolone derivatives are converted in nine steps, among them a surprisingly regioselective Baeyer-Villiger reaction, to (-)-kainic acid.

Original languageEnglish
Pages (from-to)4727-4733
Number of pages7
JournalTetrahedron
Volume58
Issue number23
Early online date12 Apr 2002
DOIs
Publication statusPublished - 3 Jun 2002

Keywords

  • Cyclization
  • Kainic acid
  • Lithium amide
  • Organolithium
  • Stereoselective

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