A radical cyclisation approach to pyroglutamates

K Goodall, A F Parsons

Research output: Contribution to journalArticlepeer-review

Abstract

Treatment of serine-derived N-(alpha-haloacetamido)dehydroalanine derivatives with tributyltin hydride in boiling benzene or toluene afforded pyroglutamates in 47-84% yield. The radical cyclisation reaction, which proceeded regioselectively in a disfavoured 5-endo-trig manner, was found to be most efficient when dichloro- and trichloroamides were employed as starting materials. Copyright (C) 1996 Elsevier Science Ltd

Original languageEnglish
Pages (from-to)6739-6758
Number of pages20
JournalTetrahedron
Volume52
Issue number19
Publication statusPublished - 6 May 1996

Keywords

  • CHIRAL STARTING MATERIAL
  • N-ALLYLTRICHLOROACETAMIDES
  • CHIROSPECIFIC SYNTHESES
  • (L)-PYROGLUTAMIC ACID
  • GLUTAMIC-ACID
  • GAMMA-LACTAMS
  • AMINO-ACIDS
  • ACETIC-ACID
  • CYCLIZATION
  • 5-ENDO-TRIG

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