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α-Arylation of α-Amino Acid Derivatives with Arynes via Memory of Chirality: Asymmetric Synthesis of Benzocyclobutenones with Tetrasubstituted Carbon.

Koji KasamatsuTomoyuki YoshimuraAttila MandiTohru TaniguchiKenji MondeTakumi FurutaTakeo Kawabata
Published in: Organic letters (2017)
A method for asymmetric α-arylation of α-amino acid derivatives via memory of chirality has been developed. Addition of axially chiral enolates, generated from α-amino acid derivatives, to in situ generated arynes, followed by intramolecular C-acylation of the resulting aryl metallic species, gave benzocyclobutenones with a tetrasubstituted carbon with retention of configuration in up to 99% ee.
Keyphrases
  • amino acid
  • structure activity relationship
  • working memory
  • ionic liquid
  • mass spectrometry
  • capillary electrophoresis
  • genetic diversity
  • walled carbon nanotubes