Activation of carboxyl groups by diphenyl 2-oxo-3-oxazolinylphosphonate. Facile preparation of versatile reagents, 3-acyl-2-oxazolones

Takehisa Kunieda, Tsunehiko Higuchi, Yoshihiro Abe, Masaaki Hirobe

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Synthetic utility of the 2-oxazolone moiety as an excellent new leaving group is described. Based on such a function of the heterocycles, diphenyl 2-oxo-3-oxazolinylphosphonate [DPPOx] has been newly introduced as a carboxyl-activating reagent which permits a facile direct preparation of 3-acyl-2-oxazolones and amides including peptides from a wide variety of carboxylic acids The 3-acyl-2-oxazolides also serve as versatile reactive agents for highly chemoselective acyl-transfer to the nucleophilic species such as amines, alcohols and thiols, providing convenient and high-yield routes to amides, esters and thiol esters under mild conditions. They are also useful intermediates for ketones and alcohols.

Original languageEnglish
Pages (from-to)3253-3260
Number of pages8
JournalTetrahedron
Volume39
Issue number20
DOIs
Publication statusPublished - 1983

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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