Enantioselective Synthesis of Dihydropyrazoles by Palladium/Xu‐Phos‐Catalyzed Alleneamination of β,γ‐Unsaturated Hydrazones with Propargylic Acetates

The palladium‐catalyzed asymmetric carboamination reaction is one of the most significant transformations in organic chemistry. Herein, we report the first palladium‐catalyzed asymmetric alleneamination of β,γ‐unsaturated hydrazones with propargylic acetates. This protocol enables the efficient inst...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-05, Vol.62 (20), p.e202300309-n/a
Main Authors: Zhang, Shuting, Wu, Shuaijie, Wang, Qiang, Xu, Shiji, Han, Ying, Yan, Chao‐Guo, Zhang, Junliang, Wang, Lei
Format: Article
Language:English
Subjects:
Acetates
Acetic acid
Allene
Asymmetry
Carboamination Reaction
Chiral Dihydropyrazoles
Enantiomers
Hydrazones
Organic chemistry
Palladium
Phosphine
Phosphines
Stereoselectivity
Substrates
Xu-Phos
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Summary:The palladium‐catalyzed asymmetric carboamination reaction is one of the most significant transformations in organic chemistry. Herein, we report the first palladium‐catalyzed asymmetric alleneamination of β,γ‐unsaturated hydrazones with propargylic acetates. This protocol enables the efficient installation of various multisubstituted allene groups onto dihydropyrazoles in good yields with excellent enantioselectivities. The chiral sulfinamide phosphine ligand Xu‐5 exhibits highly efficient stereoselective control in this protocol. The salient features of this reaction include the readily available starting materials, a broad substrate scope, an easy scale‐up, mild reaction conditions and versatile transformations. A new robust palladium‐catalyzed enantioselective alleneamination reaction of β,γ‐unsaturated hydrazones with propargylic acetates is described. The salient features of this reaction include general substrate scope, good functional group tolerance, good yields and high enantioselectivities.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202300309