Intramolecular Diels-Alder reaction of N-allyl 2-furoyl amides: Effect of steric strain and amide rotational isomerism

Masashi Nakamura, Isao Takahashi, Shunsuke Yamada, Yasuo Dobashi, Osamu Kitagawa

研究成果: Article

20 被引用数 (Scopus)

抄録

Intramolecular Diels-Alder reactions of various N-allyl 2-furoyl amides with different substituents on the nitrogen atom were investigated. The reaction of amides having bulky substituents proceeded at a faster rate than the analogs whose substituents were of less bulkiness. From the systematic experimental survey of the substituent effects and the energetic evaluation based on the DFT calculations at the B3LYP/6-31G(d) level, the enhanced reactivity was ascribed to the relief of steric strain upon cyclization rather than the amide rotational isomerism governed by the bulky substituents.

本文言語English
ページ(範囲)53-55
ページ数3
ジャーナルTetrahedron Letters
52
1
DOI
出版ステータスPublished - 2011 1 5

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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