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Practical Stereoselective Synthesis of C3‐Spirooxindole‐ and C2‐Spiropseudoindoxyl‐Pyrrolidines via Organocatalyzed Pictet‐Spengler Reaction/Oxidative Rearrangement Sequence
Author(s) -
Kondo Masaru,
Matsuyama Naoki,
Aye Tin Z.,
Mattan Irshad,
Sato Tomoyuki,
Makita Yoshinori,
Ishibashi Masami,
Arai Midori A.,
Takizawa Shinobu,
Sasai Hiroaki
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001472
Subject(s) - chemistry , tryptamines , stereoselectivity , enantioselective synthesis , pictet–spengler reaction , combinatorial chemistry , organocatalysis , organic chemistry , stereochemistry , catalysis , tryptamine , biochemistry
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®). 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.