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

研究成果: Article査読

38 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)3253-3260
ページ数8
ジャーナルTetrahedron
39
20
DOI
出版ステータスPublished - 1983

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

フィンガープリント

「Activation of carboxyl groups by diphenyl 2-oxo-3-oxazolinylphosphonate. Facile preparation of versatile reagents, 3-acyl-2-oxazolones」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル