β-Substituted Alkenyl Heteroarenes as Dipolarophiles in the Cu(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides Empowered by a Dual Activation Strategy: Stereoselectivity and Mechanistic Insight
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Title
β-Substituted Alkenyl Heteroarenes as Dipolarophiles in the Cu(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides Empowered by a Dual Activation Strategy: Stereoselectivity and Mechanistic Insight
Authors
Keywords
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Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 9, Pages 3519-3535
Publisher
American Chemical Society (ACS)
Online
2021-03-02
DOI
10.1021/jacs.0c12911
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Note: Only part of the references are listed.- Catalytic Asymmetric Reactions with N-Metallated Azomethine Ylides
- (2020) Liang Wei et al. ACCOUNTS OF CHEMICAL RESEARCH
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- (2020) Yuhong Yang et al. Nature Communications
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- (2019) Song-Bai Wu et al. ORGANIC LETTERS
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- (2019) Xin Chang et al. ORGANIC LETTERS
- Ag(I)-Fesulphos-Catalyzed Enantioselective Synthesis of 3-Silylproline Derivatives
- (2019) Raghunath Chowdhury et al. JOURNAL OF ORGANIC CHEMISTRY
- P-Stereogenic Phosphines Directed Copper(I)-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions
- (2019) Zhenjie Gan et al. ORGANIC LETTERS
- Copper-Catalyzed Regio- and Diastereoselective 1,3-Dipolar Cycloaddition Reactions of Glycine Imino Esters with 1-Propene-1,3-sultone
- (2019) Shohei Furuya et al. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- 1,3-Dipolar Cycloadditions of Stabilized Azomethine Ylides and Electrophilic Alkenes Mediated by a Recyclable TSIL·AgOAc Catalyst
- (2019) David Lledó et al. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- Switching Diastereoselectivity in Catalytic Enantioselective (3 + 2) Cycloadditions of Azomethine Ylides Promoted by Metal Salts and Privileged Segphos Derived Ligands
- (2019) Guilherme S. Caleffi et al. JOURNAL OF ORGANIC CHEMISTRY
- Towards the online computer-aided design of catalytic pockets
- (2019) Laura Falivene et al. Nature Chemistry
- Development of an Enantioselective [3 + 2] Cycloaddition To Synthesize the Pyrrolidine Core of ABBV-3221 on Multikilogram Scale
- (2019) John Hartung et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Diastereodivergent Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides and β-Fluoroalkyl Vinylsulfones: Low Copper(II) Catalyst Loading and Theoretical Studies
- (2019) Feng Cheng et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Discovery of ABBV/GLPG-3221, a Potent Corrector of CFTR for the Treatment of Cystic Fibrosis
- (2019) Marc J. C. Scanio et al. ACS Medicinal Chemistry Letters
- Enantioselective Synthesis of Fused Polycyclic Tropanes via Dearomative [3 + 2] Cycloaddition Reactions of 2-Nitrobenzofurans
- (2019) Zhen Wang et al. ORGANIC LETTERS
- Catalytic asymmetric construction of spiropyrrolidines via 1,3-dipolar cycloaddition of azomethine ylides
- (2018) Xin Fang et al. ORGANIC & BIOMOLECULAR CHEMISTRY
- A Molecular Electron Density Theory Study of the Role of the Copper Metalation of Azomethine Ylides in [3 + 2] Cycloaddition Reactions
- (2018) Luis R. Domingo et al. JOURNAL OF ORGANIC CHEMISTRY
- Palladium-Catalyzed Enantioselective Intramolecular Dearomative Heck Reaction
- (2018) Xiang Li et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Well-Designed Phosphine–Urea Ligand for Highly Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Methacrylonitrile: A Combined Experimental and Theoretical Study
- (2018) Yang Xiong et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Reaction Mechanism of Cu(I)-Mediated Reductive CO2 Coupling for the Selective Formation of Oxalate: Cooperative CO2 Reduction To Give Mixed-Valence Cu2(CO2•–) and Nucleophilic-Like Attack
- (2017) Jialing Lan et al. INORGANIC CHEMISTRY
- Nickel-catalyzed asymmetric hydrogenation of β-acylamino nitroolefins: an efficient approach to chiral amines
- (2017) Wenchao Gao et al. Chemical Science
- Highly enantioselective catalytic synthesis of chiral pyridines
- (2017) Ravindra P. Jumde et al. Nature Communications
- Catalytic Control in Cyclizations: From Computational Mechanistic Understanding to Selectivity Prediction
- (2016) Qian Peng et al. ACCOUNTS OF CHEMICAL RESEARCH
- New Mechanistic Insights on the Selectivity of Transition-Metal-Catalyzed Organic Reactions: The Role of Computational Chemistry
- (2016) Xinhao Zhang et al. ACCOUNTS OF CHEMICAL RESEARCH
- Alkenyl Arenes as Dipolarophiles in Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides
- (2016) Ana Pascual-Escudero et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Ligand-controlled stereodivergent 1,3-dipolar cycloaddition of azomethine ylides with 3-methyl-4-nitro-5-styrylisoxazoles
- (2016) Kang Liu et al. CHEMICAL COMMUNICATIONS
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- (2016) Xiaoyong Zhang et al. CHEMISTRY-A EUROPEAN JOURNAL
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- (2016) Lianhe Shu et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
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- (2016) R. P. Jumde et al. SCIENCE
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- (2015) Takuya Hashimoto et al. CHEMICAL REVIEWS
- A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry
- (2015) Rangappa S. Keri et al. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
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- (2011) Tsuyoshi Miura et al. SYNLETT
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- Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazoles
- (2010) Dalip Kumar et al. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
- Direct Asymmetric Aldol Reaction with Recyclable Fluorous Organocatalyst
- (2010) Tsuyoshi Miura et al. ORGANIC LETTERS
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- (2009) Hun Young Kim et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2008) Thomas D. Penning et al. BIOORGANIC & MEDICINAL CHEMISTRY
- Theory of 1,3-Dipolar Cycloadditions: Distortion/Interaction and Frontier Molecular Orbital Models
- (2008) Daniel H. Ess et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Indolizidine and quinolizidine alkaloids
- (2007) Joseph P. Michael NATURAL PRODUCT REPORTS
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