Practical Stereoselective Synthesis of C3-Spirooxindole- and C2-Spiropseudoindoxyl-Pyrrolidines via Organocatalyzed Pictet-Spengler Reaction/Oxidative Rearrangement Sequence

Masaru Kondo, Naoki Matsuyama, Tin Z. Aye, Irshad Mattan, Tomoyuki Sato, Yoshinori Makita, Masami Ishibashi, Midori A. Arai, Shinobu Takizawa, Hiroaki Sasai

研究成果: Article査読

3 被引用数 (Scopus)

抄録

A stereoselective synthetic route to chiral C3-spirooxindole- and C2-spiropseudoindoxyl-pyrrolidines was accomplished by an enantioselective organocatalyzed Pictet-Spengler reaction of tryptamines and isotryptamines followed by a diastereoselective oxidative rearrangement using eco-friendly oxidants (i. e., NaOCl ⋅ 5H2O and Oxone®). This sequential reaction enables rapid access to chiral C3-spirooxindole- and C2-spiropseudoindoxyl-pyrrolidines in a one-pot process. A Wnt signaling inhibitory assay of the prepared enantioenriched spiro compounds demonstrated that they exhibited moderate activities. (Figure presented.).

本文言語English
ページ(範囲)2648-2663
ページ数16
ジャーナルAdvanced Synthesis and Catalysis
363
10
DOI
出版ステータスPublished - 2021 5月 18

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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「Practical Stereoselective Synthesis of C3-Spirooxindole- and C2-Spiropseudoindoxyl-Pyrrolidines via Organocatalyzed Pictet-Spengler Reaction/Oxidative Rearrangement Sequence」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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