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

Tomoyuki Yamada, Shiori Tsukagoshi, Osamu Kitagawa

研究成果: Article査読

1 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)317-320
ページ数4
ジャーナルTetrahedron Letters
58
4
DOI
出版ステータスPublished - 2017 1 25

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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