Regiocontrolled intramolecular cyclizations of carboxylic acids to carbon-carbon triple bonds promoted by acid or base catalyst

Masanobu Uchiyama, Hiroki Ozawa, Kazuya Takuma, Yotaro Matsumoto, Mitsuhiro Yonehara, Kou Hiroya, Takao Sakamoto

研究成果: Article査読

158 被引用数 (Scopus)

抄録

We systematically investigated, for the first time, the relationship between regioselectivity and acid/base effects in the cyclization reactions between carboxylic acids and carbon-carbon triple bonds. We found novel acid- and base-promoted cyclizations to selectively give isocoumarin or pyran-2(2H)-one and phthalide or furan-2(5H)-one skeletons, respectively, and established a catalytic version of regioselective heterocyclic ring synthesis. Density functional theory calculations and application to a short route to thunberginol A were also described.

本文言語English
ページ(範囲)5517-5520
ページ数4
ジャーナルOrganic letters
8
24
DOI
出版ステータスPublished - 2006 11 23
外部発表はい

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

フィンガープリント 「Regiocontrolled intramolecular cyclizations of carboxylic acids to carbon-carbon triple bonds promoted by acid or base catalyst」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