Enantio- and Stereoselective Construction of Atisane Scaffold via Organocatalytic Intramolecular Michael Reaction and Diels-Alder Reaction

Hiroko Sekita, Kyohei Adachi, Ippei Kobayashi, Yusuke Sato, Masahisa Nakada

研究成果: Article査読

3 被引用数 (Scopus)

抄録

An enantio- and stereoselective construction of the atisane scaffold via organocatalytic intramolecular Michael reaction and Diels-Alder reaction is described. The organocatalytic intramolecular Michael reaction has been found to stereoselectively generate a trans-stereodiad comprising an all-carbon quaternary and a tertiary stereogenic centers. Use of the chiral secondary amine bearing thiourea with benzoic acid as additive is the key to obtaining the desired product with excellent ee in synthetically acceptable yield. The prepared chiral building block has been successfully converted to the compound including the atisane scaffold via the highly stereoselective intramolecular Diels-Alder reaction.

本文言語English
ページ(範囲)2390-2393
ページ数4
ジャーナルOrganic Letters
19
9
DOI
出版ステータスPublished - 2017 5 5

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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