Nucleophilic addition to N-alkoxyamides

研究成果: Review article査読

73 被引用数 (Scopus)

抄録

An amide group is one of the most abundant functional groups in organic synthesis. However, nucleophilic addition to amide carbonyls has received less attention than their construction due to their high stability. In this Perspective, we describe our recent progress with N-alkoxyamides. Incorporation of an N-alkoxy group as a reactivity control element into the nitrogen atom of an amide successfully overcomes issues inherent to the nucleophilic addition. The reaction can introduce two different nucleophiles in a one-pot process, giving a variety of substituted amines. When the Schwartz reagent was used in the first reduction step, high chemoselectivity was observed in the presence of sensitive functional groups such as esters, which resulted in the concise total synthesis of (±)-gephyrotoxin.

本文言語English
ページ(範囲)3147-3150
ページ数4
ジャーナルOrganic and Biomolecular Chemistry
12
20
DOI
出版ステータスPublished - 2014 5月 28

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

フィンガープリント

「Nucleophilic addition to N-alkoxyamides」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