☆ 4.6 Article

Highly Regio- and Enantioselective Cu/Pd Co-Catalyzed Allylic Alkylation of alpha-pyridyl-alpha-fluoroesters: Construction of Quaternary C-F Stereocenters

CHEMISTRY-AN ASIAN JOURNAL (2023)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Review Chemistry, Physical

Asymmetric transformations enabled by synergistic dual transition-metal catalysis

Liang Wei et al.

Summary: Synergistic dual transition-metal catalysis has gained increasing prominence in the enantioselective construction of chemical bonds, showing greater reactivity, selectivity, and efficiency than traditional mono-transition-metal catalysis. This review presents recent examples of asymmetric reactions enabled by synergistic dual metal catalysis, discussing the mechanism, kinetics, and selectivity in detail to showcase the cooperative and independent action of two distinct transition-metal complexes.

CHEM CATALYSIS (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Unified and Desymmetric Approach to Chiral Tertiary Alkyl Halides

Yin Zheng et al.

Summary: This study reports a reductive desymmetrization of halomalonic esters using dinuclear zinc catalysts. The resulting α-halo-β-hydroxyesters serve as important intermediates for the synthesis of drug analogs and polyhalogenated monoterpenes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Review Chemistry, Organic

Synthesis of oxindoles bearing a stereogenic 3-fluorinated carbon center from 3-fluorooxindoles

Yong-Liang Liu et al.

Summary: 3,3-Disubstituted oxindoles with a stereogenic 3-fluorinated carbon center are important structural motifs in bioactive molecules. The functionalization of 3-fluorooxindoles is a powerful method for synthesizing 3-fully substituted 3-fluorooxindoles, with many papers published on this topic in the past decade. Asymmetric catalytic methods have been developed for the enantioselective synthesis of these valuable compounds.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Organic

Modular Access to 2-(Trifluoromethyl)pyrazolo[1,5-a]pyridines and Their Benzo Analogues through a Copper(I)-Catalyzed Radical Annulation

Zhenhui Wang et al.

Summary: This paper describes a mechanistically distinctive copper-catalyzed radical annulation reaction that can synthesize valuable 2-(trifluoromethyl)pyrazolo[1,5a]pyridines and their benzo analogues. This complementary process allows the synthesis of 4- or 6-substituted target molecules as a single product, which was previously challenging to access.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synergistic Catalysis with Azomethine Ylides

Liang Wei et al.

Summary: Azomethine ylides are important intermediates for the construction of chiral N-containing compounds. Through synergistic catalysis and azomethine ylide chemistry, novel catalytic systems have been developed to convert readily available azomethine ylides into high-valued molecules. The synergistic catalyst system shows enhanced catalytic efficiency and chiral induction ability compared to traditional mono-catalysis, and can be applied in the synthesis of bioactive compounds and natural products.

CHINESE JOURNAL OF CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

Asymmetric α-Functionalization of 2-Alkyl Azaarenes: Synthesis of Tertiary Fluorides Having Vicinal Stereogenic Centers

Arko Das et al.

Summary: An enantioselective approach for synthesizing fluorinated azaarenes with vicinal quaternary-tertiary stereocenters has been summarized, utilizing a chiral copper(I)-phosphine complex to bind with the azaarenes followed by Michael addition to unsaturated acyl imidazoles, resulting in highly enantioselective compounds with excellent yields. Further functionalization of the acyl imidazole part has also been demonstrated.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Stereodivergent Synthesis of Tertiary Fluoride-Tethered Allenes via Copper and Palladium Dual Catalysis

Shao-Qian Yang et al.

Summary: The protocol describes the unprecedented stereodivergent synthesis of tertiary fluoride-tethered allenes with a stereogenic center and stereogenic axis via Cu/Pd synergistic catalysis. A wide range of conjugated enynes are coupled with various alpha-fluoroesters in high yields and diastereoselectivity. The novel stereodivergent axial-to-central chirality transfer process enables precise access to the corresponding four stereoisomers of fluorinated hydrofurans.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Iridium-Catalyzed Allylation of Nitroalkanes: Entry to β-Stereogenic α-Quaternary Primary Amines

Woo-Ok Jung et al.

Summary: The systematic study of simple nitronate nucleophiles in iridium-catalyzed allylic alkylation demonstrates the synthesis of beta-stereogenic alpha-quaternary primary amines. DFT calculations reveal early transition states and distinct trans-effects of diastereomeric chiral-at-iridium pi-allyl complexes in facilitating the formation of congested tertiary-quaternary C-C bonds.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Physical

Nickel/Enamine Cooperative Catalysis Enables Highly Enantioselective Allylic Alkylation of α-Branched Aldehydes

Wen-Qian Zhang et al.

Summary: All-carbon quaternary stereocenters are important components of natural products and bioactive compounds, and a nickel and chiral amine cooperative catalysis has been disclosed to enable highly enantioselective allylic alkylation reactions. This method allows for the synthesis of diverse compounds with excellent enantioselectivity, and has been demonstrated in the synthesis of key chiral building blocks for bioactive compounds such as (+)-eptazocine and (-)-aphanorphine.

ACS CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synergistic Cu/Pd-catalyzed asymmetric allylation: a facile access to α-quaternary cysteine derivatives

Hui-Min Wu et al.

Summary: An efficient synthetic methodology was developed to access biologically important and synthetically useful alpha-quaternary cysteine derivatives via asymmetric catalytic alpha-allylation. A wide array of alpha-quaternary cysteine derivatives were obtained with good to excellent enantioselectivities, and gram-scale asymmetric allylation was performed to maintain high yields. Additionally, synthetic transformations to access chiral spirocyclic compounds proceeded smoothly, demonstrating the utility of this methodology.

CHEMICAL COMMUNICATIONS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Sequence-Dependent Stereodivergent Allylic Alkylation/Fluorination of Acyclic Ketones

Xi-Jia Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Acyclic Branched α-Fluoro Ketones for the Direct Asymmetric Mannich Reaction Leading to the Synthesis of β-Tetrasubstituted β-Fluoro Amines

Barry M. Trost et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Organic

Enantioselective Mannich Reactions of 3-Fluorooxindoles with Cyclic N-Sulfamidate Aldimines

Jianbo Zhao et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Stereodivergent Construction of Tertiary Fluorides in Vicinal Stereogenic Pairs by Allylic Substitution with Iridium and Copper Catalysts

Zhi-Tao He et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Stereodivergent Coupling of 1,3-Dienes with Aldimine Esters Enabled by Synergistic Pd and Cu Catalysis

Qinglong Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Direct heterobenzylic fluorination, difluorination and trifluoromethylthiolation with dibenzenesulfonamide derivatives

Michael Meanwell et al.

CHEMICAL SCIENCE (2018)

添加到收藏夹

Article Multidisciplinary Sciences

Identification of a novel 2-oxindole fluorinated derivative as in vivo antitumor agent for prostate cancer acting via AMPK activation

Alicia Bort et al.

SCIENTIFIC REPORTS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles

Kaluvu Balaraman et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Article Chemistry, Organic

A Systematic Evaluation of the N-F Bond Strength of Electrophilic N-F Reagents: Hints for Atomic Fluorine Donating Ability

Jin-Dong Yang et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Stereoselective and Site-Specific Allylic Alkylation of Amino Acids and Small Peptides via a Pd/Cu Dual Catalysis

Xiaohong Huo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Allylic Alkylation with Diarylmethane Pronucleophiles: Reaction Development and Mechanistic Insights

Sheng-Chun Sha et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Convenient Late-Stage Fluorination of Pyridylic C-H Bonds with N-Fluorobenzenesulfonimide

Michael Meanwell et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

添加到收藏夹

Review Chemistry, Multidisciplinary

Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II-III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas

Yu Zhou et al.

CHEMICAL REVIEWS (2016)

添加到收藏夹

Article Chemistry, Organic

Comprehensive Energetic Scale for Quantitatively Estimating the Fluorinating Potential of N-F Reagents in Electrophilic Fluorinations

Xiao-Song Xue et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination

Victoria J. Garza et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

添加到收藏夹

Article Chemistry, Organic

Stereoselective Synthesis of α-Fluoro-γ-nitro Thioesters under Organocatalytic Conditions

Elena Cosimi et al.

ORGANIC LETTERS (2016)

添加到收藏夹

Review Chemistry, Multidisciplinary

Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates

Nicholas A. Butt et al.

CHEMICAL SOCIETY REVIEWS (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Divergent Gold(I)-Catalyzed Skeletal Rearrangements of 1,7-Enynes

Rebecca Meiss et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

添加到收藏夹

Article Chemistry, Medicinal

Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals

Edon Vitaku et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Organic

Enantioselective Pd-Catalyzed Allylation of Acyclic α-Fluorinated Ketones

Wengui Wang et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Organic

Asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates with α-fluoro-β-keto esters

Lin Yan et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Raising the pKa Limit of Soft Nucleophiles in Palladium-Catalyzed Allylic Substitutions: Application of Diarylmethane Pronucleophiles

Sheng-Chun Sha et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

添加到收藏夹

Article Pharmacology & Pharmacy

DIFLUPREDNATE FOR INFLAMMATORY EYE DISORDERS

L. Mulki et al.

DRUGS OF TODAY (2011)

添加到收藏夹

Article Chemistry, Multidisciplinary

Silica gel-mediated rearrangement of allylic acetates. Application to the synthesis of 1,3-enynes

Anna Serra-Muns et al.

CHEMICAL COMMUNICATIONS (2010)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of a Chiral Quaternary Carbon Center Bearing a Fluorine Atom: Enantio- and Diastereoselective Guanidine-Catalyzed Addition of Fluorocarbon Nucleophiles

Zhiyong Jiang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

添加到收藏夹

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective Benzylic Allylation of 2-Substituted Pyridines

Barry M. Trost et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

添加到收藏夹

Review Chemistry, Multidisciplinary

Fluorine in medicinal chemistry

Sophie Purser et al.

CHEMICAL SOCIETY REVIEWS (2008)

添加到收藏夹

Article Chemistry, Organic

[(NHC)AuI]-Catalyzed rearrangement of allylic acetates

Nicolas Marion et al.

ORGANIC LETTERS (2007)

添加到收藏夹

Article Chemistry, Medicinal

Design, synthesis, and antiviral activity of 2′-deoxy-2′-fluoro-2′-C-methylcytidine, a potent inhibitor of hepatitis C virus replication

JL Clark et al.

JOURNAL OF MEDICINAL CHEMISTRY (2005)

添加到收藏夹

Article Chemistry, Medicinal

Biological evaluation of 2-aryl-2-fluoropropionic acids as possible platforms for new medicinal agents

Y Takeuchi et al.

CHEMICAL & PHARMACEUTICAL BULLETIN (2005)

添加到收藏夹

Review Chemistry, Multidisciplinary

Thiopeptide antibiotics

MC Bagley et al.

CHEMICAL REVIEWS (2005)

添加到收藏夹

Review Chemistry, Organic

Asymmetric allylic alkylation, an enabling methodology

BM Trost

JOURNAL OF ORGANIC CHEMISTRY (2004)

添加到收藏夹

Article Chemistry, Organic

De novo synthesis of substituted pyridines

GD Henry

TETRAHEDRON (2004)

添加到收藏夹

Article Biochemistry & Molecular Biology

Targeting acute ischemic stroke with a calcium-sensitive opener of maxi-K potassium channels

VK Gribkoff et al.

NATURE MEDICINE (2001)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.