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

Kenji Shirokane, Kurosaki Yusuke, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticle

66 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

Fingerprint

Amides
Ions
Organometallics
Hydrides
methoxyamine
diisobutylaluminum

Keywords

  • Allylation
  • Amides
  • Cyanation
  • Cyclization
  • Macrocycles

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

A direct entry to substituted n-methoxyamines from n-methoxyamides via n-oxyiminium ions. / Shirokane, Kenji; Yusuke, Kurosaki; Satou, Takaaki; Chida, Noritaka.

In: Angewandte Chemie - International Edition, Vol. 49, No. 36, 23.08.2010, p. 6369-6372.

Research output: Contribution to journalArticle

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