1335207-75-4Relevant academic research and scientific papers
Practical Stereoselective Synthesis of C3-Spirooxindole- and C2-Spiropseudoindoxyl-Pyrrolidines via Organocatalyzed Pictet-Spengler Reaction/Oxidative Rearrangement Sequence
Kondo, Masaru,Matsuyama, Naoki,Aye, Tin Z.,Mattan, Irshad,Sato, Tomoyuki,Makita, Yoshinori,Ishibashi, Masami,Arai, Midori A.,Takizawa, Shinobu,Sasai, Hiroaki
, p. 2648 - 2663 (2021/04/02)
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.).
Thiourea-catalyzed enantioselective iso-pictet-spengler reactions
Lee, Yunmi,Klausen, Rebekka S.,Jacobsen, Eric N.
, p. 5564 - 5567 (2011/12/03)
A one-pot condensation of isotryptamines and aldehydes that affords enantiomerically enriched 4-substituted tetrahydro-γ-carbolines is reported. The reaction is induced by a chiral thiourea/benzoic acid dual catalyst system. Purification of the N-Boc-prot
