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

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
DOIs
Publication statusAccepted/In press - 2021

Keywords

  • Green oxidant
  • One-pot synthesis
  • Spiro compound
  • Squaramide catalyst
  • Wnt signaling inhibitory activity

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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