4.7 Article

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

期刊

ADVANCED SYNTHESIS & CATALYSIS
卷 363, 期 10, 页码 2648-2663

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202001472

关键词

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

资金

  1. JSPS KAKENHI [JP18 K14221, JP18KK0154]
  2. JST CREST [JPMJCR20R1]
  3. Iketani Science and Technology Foundation
  4. Research Foundation for Opto-Science and Technology
  5. Daiichi Sankyo Foundation of Life
  6. Hoansha Foundation
  7. Iwatani foundation
  8. AIRC

向作者/读者索取更多资源

A stereoselective synthetic route to chiral C3-spirooxindole- and C2-spiropseudoindoxyl-pyrrolidines was successfully achieved by an enantioselective organocatalyzed Pictet-Spengler reaction followed by a diastereoselective oxidative rearrangement. The prepared enantioenriched spiro compounds demonstrated moderate activities in a Wnt signaling inhibitory assay. Eco-friendly oxidants were used in the process, enabling rapid access to the chiral compounds.
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 . 5H(2)O and Oxone (R)). 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.

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