Lewis acid promoted, O-selective, nucleophilic addition of silyl enol ethers to N=O bonds

Norie Momiyama, Hisashi Yamamoto

Research output: Contribution to journalArticlepeer-review

85 Citations (Scopus)

Abstract

Not N-adduct but O-adduct is formed in the Lewis acid catalyzed nucleophilic addition of silyl enol ethers 2 to the N=O bond of nitrosobenzene (1). Various Lewis acids (e.g. alkylsilyl triflates) efficiently catalyze the formation of the aminooxy ketone (O-adduct 3) rather than of the hydroxyamino ketone (N-adduct 4), which is the product of the uncatalyzed reaction.

Original languageEnglish
Pages (from-to)2986-2988
Number of pages3
JournalAngewandte Chemie - International Edition
Volume41
Issue number16
DOIs
Publication statusPublished - 2002 Aug 16

Keywords

  • Lewis acids
  • Nitroso compounds
  • Nucleophilic addition
  • Silyl enol ethers
  • Synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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