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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Published inAngewandte Chemie International Edition Vol. 62; no. 20; pp. e202300309 - n/a
Main Authors Zhang, Shuting, Wu, Shuaijie, Wang, Qiang, Xu, Shiji, Han, Ying, Yan, Chao‐Guo, Zhang, Junliang, Wang, Lei
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 08.05.2023
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Acetates
Acetic acid
Allene
Asymmetry
Carboamination Reaction
Chemistry
Chemistry, Multidisciplinary
Chiral Dihydropyrazoles
Enantiomers
Hydrazones
Organic chemistry
Palladium
Phosphine
Phosphines
Physical Sciences
Science & Technology
Stereoselectivity
Substrates
Xu-Phos
CARBOAMINATION REACTIONS
TETRASUBSTITUTED ALLENES
ASYMMETRIC-SYNTHESIS
NATURAL-PRODUCTS
Xu-Phos
EFFICIENT SYNTHESIS
Chiral Dihydropyrazoles
Palladium
AZOMETHINE IMINES
Allene
1,3-DIPOLAR CYCLOADDITION
Carboamination Reaction
CARBOHETEROFUNCTIONALIZATION
BOND
PYRAZOLIDINES
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Abstract 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.
AbstractList 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.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.
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.
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.
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.
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 beta,gamma-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.
Author Han, Ying
Yan, Chao‐Guo
Wang, Lei
Wang, Qiang
Wu, Shuaijie
Zhang, Junliang
Xu, Shiji
Zhang, Shuting
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  email: lei.wang@yzu.edu.cn
  organization: Yangzhou University
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Issue 20
Keywords CARBOAMINATION REACTIONS
TETRASUBSTITUTED ALLENES
ASYMMETRIC-SYNTHESIS
NATURAL-PRODUCTS
Xu-Phos
EFFICIENT SYNTHESIS
Chiral Dihydropyrazoles
Palladium
AZOMETHINE IMINES
Allene
1,3-DIPOLAR CYCLOADDITION
Carboamination Reaction
CARBOHETEROFUNCTIONALIZATION
BOND
PYRAZOLIDINES
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SSID ssj0028806
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Snippet The palladium‐catalyzed asymmetric carboamination reaction is one of the most significant transformations in organic chemistry. Herein, we report the first...
The palladium-catalyzed asymmetric carboamination reaction is one of the most significant transformations in organic chemistry. Herein, we report the first...
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StartPage e202300309
SubjectTerms Acetates
Acetic acid
Allene
Asymmetry
Carboamination Reaction
Chemistry
Chemistry, Multidisciplinary
Chiral Dihydropyrazoles
Enantiomers
Hydrazones
Organic chemistry
Palladium
Phosphine
Phosphines
Physical Sciences
Science & Technology
Stereoselectivity
Substrates
Xu-Phos
Title Enantioselective Synthesis of Dihydropyrazoles by Palladium/Xu‐Phos‐Catalyzed Alleneamination of β,γ‐Unsaturated Hydrazones with Propargylic Acetates
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202300309
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000963206100001
https://www.ncbi.nlm.nih.gov/pubmed/36896746
https://www.proquest.com/docview/2808469906
https://www.proquest.com/docview/2786097769
Volume 62
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