4.7 Article

Synthesis of Chiral a-Amino Ketones via Transition Metal Catalyzed or Photoredox Cross-Coupling and Olefin Photo-Cleavage Reaction Sequence

Related references

Note: Only part of the references are listed.
Article Chemistry, Organic

Synthesis and Structural Characterization of β-Turn Mimics Containing (Z)-Chloroalkene Dipeptide Isosteres

Yuki Kodama et al.

Summary: This study presents the synthetic, spectroscopic, crystallographic, and computational analysis of a series of peptidomimetics containing L-Xaa-D-Yaa-type (Z)-chloroalkene dipeptide isosteres (CADIs). It is found that the 1,3-allylic strain across the chloroalkene moiety induces hyperconjugative interactions, contributing significantly to the stabilization of beta-turn structures.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Physical

Combined Photoredox and Carbene Catalysis for the Synthesis of α-Amino Ketones from Carboxylic Acids

Xiaochen Wang et al.

Summary: We report a mild and operationally simple method for the direct acylation of α-amino C(sp(3))-H bonds from carboxylic acids. The method combines carbene and photoredox catalysis and successfully synthesizes structurally diverse α-amino ketones through the cross-coupling reactions between a wide range of carboxylic acids and readily available N-alkyl anilines. This method demonstrates a broad substrate scope and compatibility with various functional groups.

ACS CATALYSIS (2022)

Review Chemistry, Applied

E/Z Photoisomerization of Olefins as an Emergent Strategy for the Control of Stereodivergence in Catalysis

Javier Corpas et al.

Summary: The stereoselective photoisomerization of olefins via Energy Transfer (EnT) sensitization has significant potential in designing catalytic stereodivergent methodologies. EnT catalysis has emerged as a powerful tool for olefin geometry control, with high functional group tolerance and multicatalytic compatibility.

ADVANCED SYNTHESIS & CATALYSIS (2022)

Review Chemistry, Multidisciplinary

Advances in the E → Z Isomerization of Alkenes Using Small Molecule Photocatalysts

Tomas Nevesely et al.

Summary: Geometrical E → Z alkene isomerization, a critical topic in organic photochemistry, has seen significant advancements in recent years. By utilizing energy transfer catalysis, directed isomerization of alkenes can be achieved. This review summarizes the progress in the field of geometric alkene isomerization enabled by energy transfer catalysis from 2000 to 2020, and discusses the reaction mechanisms, induction models, and applications in total synthesis and regioselective reactions.

CHEMICAL REVIEWS (2022)

Article Chemistry, Multidisciplinary

Bioinspired Palladium-Catalyzed Intramolecular C(sp3)-H Activation for the Collective Synthesis of Proline Natural Products

Quan-Zhe Li et al.

Summary: Bioinspired palladium-catalyzed intramolecular cyclization of amino acid derivatives containing a vinyl iodide moiety by C-H activation enabled rapid access to a wide range of functionalized proline derivatives with an exocyclic olefin. The functionalized prolines were used as intermediates for the synthesis of several natural products: lucentamycin A, oxotomaymycin, oxoprothracarcin, and barmumycin.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Organic

The regioselective Wacker oxidation of internal allylamines: synthesis of functionalized and challenging β-amino ketones

Mateusz Garbacz et al.

Summary: A convenient and general protocol for the oxidation of internal allylamine derivatives to beta-amino ketones using palladium catalyst has been reported. The reaction takes place at room temperature and demonstrates broad substrate scope, high tolerance towards functional groups and N-protecting groups. Additionally, potential applications such as synthesis of bioactive molecules and transformation of selected beta-amino ketones into other building blocks are described.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Photoinduced Oxygen Transfer Using Nitroarenes for the Anaerobic Cleavage of Alkenes

Dan E. Wise et al.

Summary: We report a new method for anaerobic cleavage of alkenes into carbonyl compounds using nitroarenes as oxygen transfer reagents under visible light. This approach is a safe and practical alternative to traditional oxidative cleavage methods. Mechanistic studies show that the transformation occurs through direct photoexcitation of the nitroarene followed by nonstereospecific radical cycloaddition with alkenes. Various alkenes with oxidatively sensitive functionalities can be efficiently and selectively cleaved anaerobically to generate carbonyl derivatives.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Multidisciplinary Sciences

Photoexcited nitroarenes for the oxidative cleavage of alkenes

Alessandro Ruffoni et al.

Summary: This study presents an alternative method for oxidative cleavage of alkenes using nitroarenes and purple-light irradiation. Photoexcited nitroarenes can effectively substitute ozone for facile radical [3+2] cycloaddition with alkenes, resulting in safe-handling 'N-doped' ozonides that lead to carbonyl products under mild hydrolytic conditions. This method allows controlled cleavage of alkenes in the presence of commonly used organic functionalities, and achieves site selectivity in substrates containing multiple alkenes by harnessing the diversity of nitroarenes.

NATURE (2022)

Article Chemistry, Organic

Visible-light-mediated defluorinative cyclization of α-fluoro-β-enamino esters catalyzed by 4-CzIPN

Yi-Fan Song et al.

Summary: The study demonstrates a mild and efficient method for the construction of indoles using 4-CzIPN as a photocatalyst and alpha-fluoro-beta-enamino esters as substrates under visible light irradiation. Mechanistic studies reveal that the formation of indoles is attributed to the triplet N-aryl enamines produced through energy transfer.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Multidisciplinary

Quaternary stereocentres via catalytic enantioconvergent nucleophilic substitution reactions of tertiary alkyl halides

Zhaobin Wang et al.

Summary: The development of efficient methods, particularly catalytic and enantioselective processes, for the construction of all-carbon quaternary stereocentres is an important and difficult challenge in organic synthesis. A nickel-based chiral catalyst has been shown to achieve enantioconvergent couplings of tertiary electrophiles with alkenylmetal nucleophiles, providing access to a variety of organic compounds with good yield and enantioselectivity. This approach offers a potentially versatile strategy for the synthesis of complex molecules, including natural product intermediates.

NATURE CHEMISTRY (2021)

Article Medicine, Research & Experimental

Development of a small molecule that corrects misfolding and increases secretion of Z alpha(1)-antitrypsin

David A. Lomas et al.

Summary: The study identified small molecules that bind to and stabilize mutant alpha(1)-antitrypsin, blocking aberrant polymerisation and increasing secretion, providing a potential treatment for deficiency. Oral dosing in transgenic mice showed a significant increase in secretion without observable clearance of hepatic inclusions, demonstrating the potential of mutation ameliorating small molecules in treating the disease.

EMBO MOLECULAR MEDICINE (2021)

Review Medicine, General & Internal

Oral Antiplatelet Therapy After Acute Coronary Syndrome: A Review

Hassan Kamran et al.

Summary: Dual antiplatelet therapy is beneficial for patients with acute coronary syndrome, and the specific combination and duration should be based on patient characteristics and bleeding risk.

JAMA-JOURNAL OF THE AMERICAN MEDICAL ASSOCIATION (2021)

Article Chemistry, Organic

Development of Methods for Convergent Synthesis of Chloroalkene Dipeptide Isosteres and Its Application

Takuya Kobayakawa et al.

Summary: This study reports improved methods for convergent synthesis using a chloroalkene dipeptide isostere (CADI), demonstrating the direct application of Fmoc-protected CADI in solid-phase peptide synthesis and the discovery of a CADI-containing peptidomimetic with superior inhibitory effects on amyloid-beta aggregation compared to the parent peptide.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

Recent advances in radical chemistry proceeding through pro-aromatic radicals

Anup Bhunia et al.

Summary: This review discusses the use of pro-aromatic compounds as carbon- and heteroatom-radical precursors, highlighting the underlying principle of gaining aromaticity for pro-aromatic radicals. The compounds can be easily transformed into radicals, which can then engage in hydrogen atom or radical functional group transfer chemistry.
Article Chemistry, Multidisciplinary

Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones

Anna Bay et al.

Summary: This study reports the light-driven synthesis of aliphatic and alpha-amino ketones using single-electron NHC operators. Computational and experimental results show that the reactivity of the key radical intermediate depends on the substrate and can be modulated through steric and electronic parameters of the NHC. This methodology is showcased in the direct late-stage functionalization of amino acids and pharmaceutical compounds, highlighting the utility of single-electron NHC operators.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Biochemistry & Molecular Biology

Pan-3C Protease Inhibitor Rupintrivir Binds SARS-CoV-2 Main Protease in a Unique Binding Mode

Gordon J. Lockbaum et al.

Summary: Rupintrivir targets the 3C cysteine proteases of picornaviruses but shows weak activity against the 3C-like protease of SARS-CoV-2. The study found that Rupintrivir binds uniquely to the active site of the SARS-CoV-2 main protease, potentially offering a novel approach to inhibiting cysteine proteases.

BIOCHEMISTRY (2021)

Article Chemistry, Medicinal

The development of highly potent and selective small molecule correctors of Z α1-antitrypsin misfolding

John Liddle et al.

Summary: α1-antitrypsin deficiency is characterized by misfolding and intracellular polymerization of mutant α1-antitrypsin protein in hepatocytes. Small molecules that stabilize Z α1-antitrypsin were identified through a DNA-encoded library screen. Subsequent structure-based optimization yielded a series of highly potent, selective, and cellular active α1-antitrypsin correctors.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2021)

Article Chemistry, Multidisciplinary

Oxidative Cleavage of Alkenes by O2 with a Non-Heme Manganese Catalyst

Zhiliang Huang et al.

Summary: The oxidative cleavage of C = C double bonds with molecular oxygen is a key transformation in chemical and pharmaceutical synthesis. While nature has efficient enzymes for this reaction, synthetic chemists face challenges in finding suitable metal catalysts. This work presents a light-driven, Mn-catalyzed method for selective oxidation of alkenes with good functional group tolerance, involving asymmetric Mn-oxo species and methanol as an activator for O-2.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Organic

Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis

Mateusz Garbacz et al.

Summary: This study presents a new method for the synthesis of allylamines through cross-coupling of alkyl bromides with 3-bromoallylamines, using a combination of photoredox and Ni catalysis. The reaction is performed under mild conditions, with blue light irradiation and a specific organic dye as a photocatalyst, enabling the construction of complex multifunctional allylamine derivatives.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids

Anna V. Bay et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Dehydrogenative Coupling of Benzylic and Aldehydic C-H Bonds

Tairin Kawasaki et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

PdII-Catalyzed Enantioselective C(sp3)-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group

Li-Jun Xiao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Physical

Decarboxylative Hydroalkylation of Alkynes via Dual Copper-Photoredox Catalysis

Marco M. Mastandrea et al.

ACS CATALYSIS (2020)

Article Chemistry, Applied

The Synthesis of Chiral Allyl Carbamates via Merger of Photoredox and Nickel Catalysis

Mateusz Garbacz et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Article Chemistry, Organic

Asymmetric Transfer Hydrogenation: Dynamic Kinetic Resolution of α-Amino Ketones

Shweta K. Gediya et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Pd(II)-Catalyzed Enantioselective γ-C(sp3)-H Functionalizations of Free Cyclopropylmethylamines

Zhe Zhuang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Chiral Phosphoric Acid Catalyzed Enantioselective Synthesis of α-Tertiary Amino Ketones from Sulfonium Ylides

Wengang Guo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Multidisciplinary Sciences

High-resolution ex vivo NMR spectroscopy of human Z α1-antitrypsin

Alistair M. Jagger et al.

NATURE COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Direct Enantioselective C(sp3)-H Acylation for the Synthesis of α-Amino Ketones

Xiaomin Shu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Enantioselective Arylation of Benzylic C-H Bonds by Copper-Catalyzed Radical Relay

Wen Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Asymmetric Total Syntheses of the Akuammiline Alkaloids (-)-Strictamine and (-)-Rhazinoline

Wenfei Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Physical

Recent Advances in Pyridinium Salts as Radical Reservoirs in Organic Synthesis

Fu-Sheng He et al.

ACS CATALYSIS (2019)

Review Chemistry, Multidisciplinary

Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling

John A. Milligan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Clinical Neurology

An update on ketamine and its two enantiomers as rapid-acting antidepressants

Kai Zhang et al.

EXPERT REVIEW OF NEUROTHERAPEUTICS (2019)

Review Chemistry, Applied

N-(Acyloxy)phthalimides as Redox-Active Esters in Cross-Coupling Reactions

Sandip Murarka

ADVANCED SYNTHESIS & CATALYSIS (2018)

Article Chemistry, Multidisciplinary

Enantioselective amine α-functionalization via palladium-catalysed C-H arylation of thioamides

Pankaj Jain et al.

NATURE CHEMISTRY (2017)

Article Chemistry, Organic

The Allyl Cyanate/Isocyanate Rearrangement: An Efficient Tool for the Stereocontrolled Formation of Allylic C-N Bonds

Pierre-Antoine Nocquet et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Multidisciplinary Sciences

Decarboxylative alkenylation

Jacob T. Edwards et al.

NATURE (2017)

Review Chemistry, Multidisciplinary

The merger of transition metal and photocatalysis

Jack Twilton et al.

NATURE REVIEWS CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Direct Acylation of C(sp3)-H Bonds Enabled by Nickel and Photoredox Catalysis

Candice L. Joe et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

Recent Advances in Transition-Metal-Free Oxygenation of Alkene C=C Double Bonds for Carbonyl Generation

Jie-Ping Wan et al.

CHEMISTRY-AN ASIAN JOURNAL (2016)

Article Multidisciplinary Sciences

Enantioselective cyanation of benzylic C-H bonds via copper-catalyzed radical relay

Wen Zhang et al.

SCIENCE (2016)

Review Chemistry, Organic

Recent Advances on Asymmetric Nitroso Aldol Reaction

Pedro Merino et al.

SYNTHESIS-STUTTGART (2016)

Editorial Material Chemistry, Organic

Photoredox sheds new light on nickel catalysis: from carbon-carbon to carbon-heteroatom bond formation

Yong-Yuan Gui et al.

ORGANIC CHEMISTRY FRONTIERS (2016)

Article Chemistry, Multidisciplinary

Direct Asymmetric Amination of α-Branched Cyclic Ketones Catalyzed by a Chiral Phosphoric Acid

Xiaoyu Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones

Dillon H. Miles et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Fragment Couplings via CO2 Extrusion-Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox

Chi Chip Le et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

A Bio-Inspired, Catalytic E → Z Isomerization of Activated Olefins

Jan B. Metternich et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Enantioselective N-H Insertion Reaction of a-Aryl a-Diazoketones: An Efficient Route to Chiral a- Aminoketones

Bin Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Palladium(II)-Catalyzed Enantioselective C(sp3)-H Activation Using a Chiral Hydroxamic Acid Ligand

Kai-Jiong Xiao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Facile Synthesis of Z-Alkenes via Uphill Catalysis

Kamaljeet Singh et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Review Chemistry, Applied

Oxidative Alkene Cleavage by Chemical and Enzymatic Methods

Aashrita Rajagopalan et al.

ADVANCED SYNTHESIS & CATALYSIS (2013)

Article Chemistry, Multidisciplinary

Development of a Chiral Bis(guanidino)iminophosphorane as an Uncharged Organosuperbase for the Enantioselective Amination of Ketones

Tadahiro Takeda et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Review Substance Abuse

Ketamine use: a review

Celia J. A. Morgan et al.

ADDICTION (2012)

Article Chemistry, Multidisciplinary

Engaging unactivated alkyl, alkenyl and aryl iodides in visible-light-mediated free radical reactions

John D. Nguyen et al.

NATURE CHEMISTRY (2012)

Article Chemistry, Organic

Synthesis of manzacidin A and C: efficient construction of quaternary carbon stereocenters bearing nitrogen substituents

Yoshiyasu Ichikawa et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2012)

Article Emergency Medicine

Clinical Practice Guideline for Emergency Department Ketamine Dissociative Sedation: 2011 Update

Steven M. Green et al.

ANNALS OF EMERGENCY MEDICINE (2011)

Article Chemistry, Multidisciplinary

New Electrophilic Addition of α-Diazoesters with Ketones for Enantioselective C-N Bond Formation

Wei Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Review Cardiac & Cardiovascular Systems

Role of Prasugrel, a Novel P2Y12 Receptor Antagonist, in the Management of Acute Coronary Syndromes

William L. Baker et al.

AMERICAN JOURNAL OF CARDIOVASCULAR DRUGS (2009)

Article Chemistry, Medicinal

Synthesis and Biological Evaluation of Bupropion Analogues as Potential Pharmacotherapies for Cocaine Addiction

F. Ivy Carroll et al.

JOURNAL OF MEDICINAL CHEMISTRY (2009)

Article Pharmacology & Pharmacy

Prasugrel: A novel antiplatelet agent

Amy B. Riley et al.

AMERICAN JOURNAL OF HEALTH-SYSTEM PHARMACY (2008)

Article Chemistry, Multidisciplinary

Asymmetric organocatalysed [1,3]-sigmatropic rearrangements

Sara Kobbelgaard et al.

CHEMISTRY-A EUROPEAN JOURNAL (2008)

Article Chemistry, Organic

Rapid Synthesis of 1,3,4,4-Tetrasubstituted β-Lactams from Methyleneaziridines Using a Four-Component Reaction

Claire C. A. Cariou et al.

JOURNAL OF ORGANIC CHEMISTRY (2008)

Article Microbiology

In vitro resistance study of rupintrivir, a novel inhibitor of human rhinovirus 3C protease

S. L. Binford et al.

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY (2007)

Review Chemistry, Multidisciplinary

Asymmetric hydrogenation of prochiral amino ketones to amino alcohols for pharmaceutical use

Franz Dietrich Klingler

ACCOUNTS OF CHEMICAL RESEARCH (2007)

Article Chemistry, Multidisciplinary

Diastereomeric fluoroolefins as peptide bond mimics prepared by asymmetric reductive amination of alpha-fluoroenones

Guillaume Dutheuil et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

Article Chemistry, Medicinal

Synthesis of novel keto-ACE analogues as domain-selective angiotensin I-converting enzyme inhibitors

Aloysius T. Nchinda et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2006)

Review Chemistry, Multidisciplinary

Ozonolysis applications in drug synthesis

Scott G. Van Ornum et al.

CHEMICAL REVIEWS (2006)

Article Chemistry, Multidisciplinary

A new family of small molecules to probe the reactivation of mutant p53

MC Myers et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Review Chemistry, Multidisciplinary

Recent advances in catalytic, enantioselective alpha aminations and alpha oxygenations of carbonyl compounds

JM Janey

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

Review Chemistry, Organic

Electrophilic α-amination of carbonyl compounds

E Erdik

TETRAHEDRON (2004)

Article Chemistry, Multidisciplinary

A short, one-pot synthesis of bupropion (Zyban®, Wellbutrin®)

DM Perrine et al.

JOURNAL OF CHEMICAL EDUCATION (2000)