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

1 引用 (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.

元の言語English
ページ(範囲)317-320
ページ数4
ジャーナルTetrahedron Letters
58
発行部数4
DOI
出版物ステータスPublished - 2017 1 25

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Anilides
Imidoesters
Anions
Alkylation
Ethers
Sulfonic Acids
Carboxylic Acids
Esters
Alcohols
2,4,6-tri-tert-butylanilide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

これを引用

Specific reactivity of 2,4,6-tri-tert-butylanilide anions and its application to benzylation reagent. / Yamada, Tomoyuki; Tsukagoshi, Shiori; Kitagawa, Osamu.

:: Tetrahedron Letters, 巻 58, 番号 4, 25.01.2017, p. 317-320.

研究成果: Article

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AB - 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.

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