@article{9dcce97051bc4f459846c58d55b70a9a,
title = "Practical Stereoselective Synthesis of C3-Spirooxindole- and C2-Spiropseudoindoxyl-Pyrrolidines via Organocatalyzed Pictet-Spengler Reaction/Oxidative Rearrangement Sequence",
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{\textregistered}). 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.",
keywords = "Green oxidant, One-pot synthesis, Spiro compound, Squaramide catalyst, Wnt signaling inhibitory activity",
author = "Masaru Kondo and Naoki Matsuyama and Aye, {Tin Z.} and Irshad Mattan and Tomoyuki Sato and Yoshinori Makita and Masami Ishibashi and Arai, {Midori A.} and Shinobu Takizawa and Hiroaki Sasai",
note = "Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP18 K14221 in Early‐Career Scientists, JP18KK0154 in Promotion of Joint International Research (Fostering Joint International Research(B)), JST CREST Grant Number JPMJCR20R1, Iketani Science and Technology Foundation, Research Foundation for Opto‐Science and Technology, Daiichi Sankyo Foundation of Life, Hoansha Foundation, Iwatani foundation and AIRC‐Grant 2019. We acknowledge the technical staff of the Comprehensive Analysis Center of ISIR, Osaka University (Japan). We thank Dr. Shun Saito for FOP‐Flash assay. We also thank Nippon Light Metal Company for providing large amount of NaOCl ⋅ 5HO. 2 Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",
year = "2021",
doi = "10.1002/adsc.202001472",
language = "English",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-VCH Verlag",
}