Specific reactivity of 2,4,6-tri-tert-butylanilide anions and its application to benzylation reagent

Tomoyuki Yamada, Shiori Tsukagoshi, Osamu Kitagawa

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Abstract

The reaction of methyl iodide with an anilide anion prepared from 2,4,6-tri-tert-butylanilide and NaH in CH3CN gave N-methyl anilide (N-alkylation product) as a major product, while in the reaction of benzyl bromide with the anilide anion in DMF, O-benzyl imidate (O-alkylation product) was obtained with almost complete selectivity. The treatment of O-benzyl imidate with alcohols and carboxylic acids in the presence of trifluoromethane sulfonic acid gave benzyl ethers and benzyl esters, respectively.

Original languageEnglish
Pages (from-to)317-320
Number of pages4
JournalTetrahedron Letters
Volume58
Issue number4
DOIs
Publication statusPublished - 2017 Jan 25

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Keywords

  • Anilides
  • Benzylation
  • Ethers
  • Imidates
  • tert-Butyl

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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