An efficient synthesis of optically active axially chiral anilide and its application to iodine-mediated asymmetric Diels-Alder reaction

Osamu Kitagawa, Hirotaka Izawa, Takeo Taguchi, Motoo Shiro

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A new axially chiral N-acryl-N-allyl-o-tert-butylanilide with high optical purity (96-97 %ee) was prepared in good yield from (S)-O-acetyl lactic acid and N-allyl o-t-butylaniline. Iodine mediated Diels-Alder reaction of the axially chiral N-acryl anilide with cyclopentadiene or isoprene proceeded with high diastereoselectivity.

Original languageEnglish
Pages (from-to)4447-4450
Number of pages4
JournalTetrahedron Letters
Issue number25
Publication statusPublished - 1997 Jun 23


ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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