Enantioselective Alkynylation of 2‐Aryl‐3H‐indol‐3‐ones via Cooperative Catalysis of Copper/Chiral Phosphoric Acid

A facile enantioselective alkynylation of cyclic ketimines attached to a neutral functional group utilizing the dual Cu(I)‐CPA catalysis is described. The strategy of the alkynylation of 2‐aryl‐3H‐indol‐3‐one directly to chiral propargylic amines containing indolin‐3‐one moiety in good yields and en...

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Bibliographic Details
Published in:Chemistry, an Asian journal an Asian journal, 2023-09, Vol.18 (18), p.e202300526-n/a
Main Authors: Wu, Xi‐Xi, Ma, Tao, Qiao, Xiu‐Xiu, Zou, Chang‐Peng, Li, Ganpeng, He, Yonghui, Zhao, Xiao‐Jing
Format: Article
Language:English
Subjects:
2-Aryl-3H-indol-3-ones
Amines
Aromatic compounds
C2-quaternary indolin-3-ones
Catalysis
Chemistry
Chiral phosphoric acids
Chiral propargylic aminles
Cooperative catalysis
Copper
Enantiomers
Functional groups
Imines
Phosphoric acid
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Summary:A facile enantioselective alkynylation of cyclic ketimines attached to a neutral functional group utilizing the dual Cu(I)‐CPA catalysis is described. The strategy of the alkynylation of 2‐aryl‐3H‐indol‐3‐one directly to chiral propargylic amines containing indolin‐3‐one moiety in good yields and enantioselectivities. Moreover, gram‐scale synthesis of chiral propargylamines based C2‐quaternary indolin‐3‐ones was performed. The synthetic applications were confirmed by transformations of the products with no decrease in the yield and enantioselectivity. Herein, we describe the enantioselective alkynylation of 2‐aryl‐3H‐indol‐3‐ones via cooperative catalysis of copper/chiral phosphoric Acid. This asymmetric reaction is amenable to a wide range of terminal alkynes or 3H‐indol‐3‐ones, providing various chiral propargylic amines with moderate to good enantioselectivities and yields.
ISSN:1861-4728
1861-471X
1861-471X
DOI:10.1002/asia.202300526