Asymmetric aza-Friedel-Crafts Reaction of Cyclic Ketimines with 5-Aminopyrazole Derivatives: Expedient Access to Pyrazole-Based C2-quaternary Indolin-3-Ones.

Chemistry

Key Laboratory of Chemistry in Ethnic Medicinal Resources, Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, State Ethnic Affairs Commission & Ministry of Education, School of Ethnic Medicine, Yunnan Minzu University, Kunming, 650500, P. R. China.

Published: April 2023

AI Article Synopsis

  • A chiral phosphoric acid catalyst is used to facilitate an enantioselective aza-Friedel-Crafts reaction between 5-aminopyrazole derivatives and cyclic ketimines.
  • This process results in the production of pyrazole-derived C2-quaternary indolin-3-ones with both high enantioselectivity and regioselectivity.
  • The reaction can be scaled up to gram quantities without losing yield or enantioselectivity, demonstrating its practical application.

Article Abstract

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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Source
http://dx.doi.org/10.1002/chem.202203914DOI Listing

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