Catalytic and selective conversion of (Z)-2-en-4-ynoic acids to either 2H-pyran-2-ones in the presence of ZnBr2 or (Z)-5-alkylidenefuran-2(5H)-ones in the presence of Ag2CO3

Luigi Anastasia, Caiding Xu, Ei Ichi Negishi

Research output: Contribution to journalArticle

Abstract

Treatment of (Z)-5-alkyl-2-en-4-ynoic acids (1), prepared by the Pd-catalyzed alkynylzinc-β-haloacrylic acid coupling, with 5-10 mol% of ZnBr2 can produce 6-alkyl-2H-pyran-2-ones (2) along with minor amounts of (Z)-5-alkylidenefuran-2(5H)-ones (3) in >90% combined yields, with often very high (≈95/5) pyranone/furanone ratios. On the other hand, lactonization of 1 catalyzed by Ag2CO3 provides a selective synthesis of (Z)-5-alkylidenefuran-2(5H)-ones (3) in >90% yields along with minor amounts (≤5%) of 2.

Original languageEnglish
Pages (from-to)5673-5676
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number32
DOIs
Publication statusPublished - Aug 5 2002

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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