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

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 an...

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Published in:Chemistry : a European journal 2023-04, Vol.29 (20), p.e202203914-n/a
Main Authors: Qiao, Xiu‐Xiu, He, Yonghui, Ma, Tao, Zou, Chang‐Peng, Wu, Xi‐Xi, Li, Ganpeng, Zhao, Xiao‐Jing
Format: Article
Language:English
Subjects:
2-aryl-3H-indol-3-ones
5-Aminopyrazoles
C2-quaternary indolin-3-ones
Chemistry
chiral phosphoric acids
dual H-bonds
Enantiomers
Friedel-Crafts reaction
Functional groups
Imines
Phosphoric acid
Pyrazole
Pyrazoles
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cited_by cdi_FETCH-LOGICAL-c3734-2418b1aa175f2e2a87de012550e9846b27bc1247e4d13d7c8e0e54a37488dab93
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container_start_page e202203914
container_title Chemistry : a European journal
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creator Qiao, Xiu‐Xiu
He, Yonghui
Ma, Tao
Zou, Chang‐Peng
Wu, Xi‐Xi
Li, Ganpeng
Zhao, Xiao‐Jing
description 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. Herein, we describe a challenging chiral phosphoric acid‐catalyzed asymmetric aza‐Friedel–Crafts reaction of 5‐aminopyrazoles with cyclic‐ketimines attached to neutral functional group, achieving enantiomerically enriched pyrazole‐based C2‐quaternary indolin‐3‐ones with highly enantioselectivities and regioselectivities.
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subjects 2-aryl-3H-indol-3-ones
5-Aminopyrazoles
C2-quaternary indolin-3-ones
Chemistry
chiral phosphoric acids
dual H-bonds
Enantiomers
Friedel-Crafts reaction
Functional groups
Imines
Phosphoric acid
Pyrazole
Pyrazoles
title Asymmetric aza‐Friedel–Crafts Reaction of Cyclic Ketimines with 5‐Aminopyrazole Derivatives: Expedient Access to Pyrazole‐Based C2‐quaternary Indolin‐3‐Ones
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