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

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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.

Original languageEnglish
Pages (from-to)53-55
Number of pages3
JournalTetrahedron Letters
Issue number1
Publication statusPublished - 2011 Jan 5


ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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