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A radical cyclisation approach to pyroglutamates

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

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

    Research areas

  • 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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