Development of a Chiral N -Alkoxyamide Strategy and Application to the Asymmetric Total Synthesis of Fasicularin

Ryo Minamikawa, Keisuke Fukaya, Akihiro Kobayashi, Yukinori Komiya, Shio Yamamoto, Daisuke Urabe, Noritaka Chida, Takaaki Sato

研究成果: Article査読

抄録

The asymmetric total synthesis of fasicularin by a chiral Nalkoxyamide strategy is reported. Incorporation of the chiral alkoxy group onto an amide nitrogen changes the original reactivity of the amide, enabling two key transformations: aza-spirocyclization and the reductive Strecker reaction. DFT calculations indicate that pyramidalization of the N-alkoxyamide nitrogen is crucial to produce a cyclic hemiaminal in equilibrium, which undergoes aza-spirocyclization. The chiral alkoxy group is also used as a stereocontrol element to establish two consecutive stereocenters. The iridium-catalyzed reductive Strecker reaction of the N-alkoxylactam provides the aminonitrile with high diastereoselectivity.

本文言語English
ページ(範囲)4621-4635
ページ数15
ジャーナルSynthesis (Germany)
53
24
DOI
出版ステータスPublished - 2021 12 17

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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