A direct entry to substituted n-methoxyamines from n-methoxyamides via n-oxyiminium ions

Kenji Shirokane, Kurosaki Yusuke, Sato Takaaki, Noritaka Chida

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

Take the direct path: Sequential nucleophilic addition of N-methoxyamides using DIBAL and organometallic reagents provided substituted N-methoxyamines in one pot via five-membered chelated intermediates (see scheme, DIBAL=diisobutylaluminum hydride). The reaction allows functionalization of acyclic amides and macrolactams without a preactivation step, which is generally required for inert amide carbonyl groups.

Original languageEnglish
Pages (from-to)6369-6372
Number of pages4
JournalAngewandte Chemie - International Edition
Volume49
Issue number36
DOIs
Publication statusPublished - 2010 Aug 23

Keywords

  • Allylation
  • Amides
  • Cyanation
  • Cyclization
  • Macrocycles

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'A direct entry to substituted n-methoxyamines from n-methoxyamides via n-oxyiminium ions'. Together they form a unique fingerprint.

  • Cite this