Nucleophilic addition to N-alkoxyamides

Research output: Contribution to journalReview article

61 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3147-3150
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number20
DOIs
Publication statusPublished - 2014 May 28

    Fingerprint

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this