Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 29, Issue 20, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202203914
Keywords
5-Aminopyrazoles; 2-aryl-3H-indol-3-ones; chiral phosphoric acids; C2-quaternary indolin-3-ones; dual H-bonds
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A chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of 5-aminopyrazole derivatives with cyclic ketimines attached to a neutral functional group is reported, giving high enantioselectivities and regioselectivities in the formation of pyrazole-based C2-quaternary indolin-3-ones. Gram-scale synthesis of the 5-aminopyrazole-based C2-quaternary indolin-3-ones was also achieved without a decrease in yield and enantioselectivity.
A chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of 5-aminopyrazole derivatives with cyclic ketimines attached to a neutral functional group is reported. This protocol allows the formation of pyrazole-based C2-quaternary indolin-3-ones with high enantioselectivities and regioselectivities. Moreover, gram-scale synthesis of the 5-aminopyrazole-based C2-quaternary indolin-3-ones was performed, with no decrease in the yield and enantioselectivity.
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