Synthesis of 9-amino(9-deoxy)epi cinchona alkaloids, general chiral organocatalysts for the stereoselective functionalization of carbonyl compounds

No abstract is available for this paper.

• Publication year

  2013

• Venue

  Nature Protocols

• Publication date

  2013-01-17

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1038/nprot.2012.155PMID 23329005
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Trienamine catalysis with 2,4-dienones: development and application in asymmetric Diels-Alder reactions.

  2012cited by this paper
• Cinchona-based primary amine catalysis in the asymmetric functionalization of carbonyl compounds.

  2012cited by this paper
• The diarylprolinol silyl ether system: a general organocatalyst.

  2012cited by this paper
• Enantioselective organocatalytic α-fluorination of cyclic ketones.

  2011cited by this paper
• Trienamines in asymmetric organocatalysis: Diels-Alder and tandem reactions.

  2011cited by this paper
• Easy Access to 9-Epimersof Cinchona Alkaloids: One-Pot Inversion by MitsunobuEsterification-Saponification

  2011cited by this paper
• Mitsunobu Inversion of a Secondary Alcohol with Diphenylphosphoryl azide. Application to the Enantioselective Multikilogram Synthesis of a HCV Polymerase Inhibitor

  2011cited by this paper
• Diastereodivergent asymmetric sulfa-Michael additions of α-branched enones using a single chiral organic catalyst.

  2011cited by this paper
• Recent advances in asymmetric catalysis with cinchona alkaloid-based primary amines

  2011influential reference
• Emil Knoevenagel and the roots of aminocatalysis.

  2010cited by this paper
• Asymmetric synthesis of a potent, aminopiperidine-fused imidazopyridine dipeptidyl peptidase IV inhibitor.

  2010cited by this paper
• Catalytic asymmetric epoxidation of alpha-branched enals.

  2010cited by this paper
• Synthesis of Amino-Bridged Oligosaccharide Mimetics

  2010cited by this paper
• Asymmetric catalytic aziridination of cyclic enones.

  2010cited by this paper
• Cooperative organocatalysis for the asymmetric γ alkylation of α-branched enals.

  2010cited by this paper
• Advances and Applications

  2010cited by this paper
• Clickable 9-azido-(9-deoxy)-Cinchona alkaloids: synthesis and conformation

  2010cited by this paper
• Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis

  2010cited by this paper
• Thio)urea Organocatalysts

  2009cited by this paper
• Asymmetric organocatalytic cascade reactions with alpha-substituted alpha,beta-unsaturated aldehydes.

  2009cited by this paper
• Targeting structural and stereochemical complexity by organocascade catalysis: construction of spirocyclic oxindoles having multiple stereocenters.

  2009cited by this paper
• Enantioselective synthesis of functionalized nitrocyclopropanes by organocatalytic conjugate addition of bromonitroalkanes to alpha,beta-unsaturated enones.

  2009cited by this paper
• Asymmetric catalysis with chiral primary amine-based organocatalysts.

  2009cited by this paper
• Organocascade reactions of enones catalyzed by a chiral primary amine.

  2009cited by this paper
• Hydrogen bonding in organic synthesis

  2009cited by this paper
• Improved Synthesis of 1-(Azidomethyl)-3,5-bis-(trifluoromethyl)benzene: Development of Batch and Microflow Azide Processes

  2009cited by this paper
• Asymmetric Organocatalytic Cascade Reactions with α‐Substituted α,β‐Unsaturated Aldehydes

  2009cited by this paper
• Asymmetric Aza‐Michael Reactions of α,β‐Unsaturated Ketones with Bifunctional Organic Catalysts.

  2009cited by this paper
• Mitsunobu and related reactions: advances and applications.

  2009cited by this paper
• Organocatalytic asymmetric vinylogous alpha-ketol rearrangement: enantioselective construction of chiral all-carbon quaternary stereocenters in spirocyclic diketones via semipinacol-type 1,2-carbon migration.

  2009cited by this paper
• A Novel Organocatalytic Tool for the Iminium Activation of a,-Unsaturated Ketones

  2008influential reference
• Catalytic enantioselective peroxidation of alpha,beta-unsaturated ketones.

  2008cited by this paper
• Catalytic Enantioselective Peroxidation of α,β‐Unsaturated Ketones.

  2008cited by this paper
• Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts.

  2008cited by this paper
• Asymmetric aza-Michael reactions of alpha,beta-unsaturated ketones with bifunctional organic catalysts.

  2008cited by this paper
• Asymmetric aminocatalysis--gold rush in organic chemistry.

  2008influential reference
• Primary-amine-catalyzed enantioselective intramolecular aldolizations.

  2008cited by this paper
• Organocatalytic asymmetric aziridination of enones.

  2008cited by this paper
• A Novel Organocatalytic Toolfor the Iminium Activation of α,β-Unsaturated Ketones

  2008cited by this paper
• Practical demethylation of aryl methyl ethers using an odorless thiol reagent

  2008cited by this paper
• Dienamine Catalysis: Organocatalytic Asymmetric ?-Amination of a,-Unsaturated Aldehydes

  2007cited by this paper
• Carbohydrate mimic of 2-deoxystreptamine for the preparation of conformationally constrained aminoglycosides

  2007cited by this paper
• Readily accessible 9-epi-amino cinchona alkaloid derivatives promote efficient, highly enantioselective additions of aldehydes and ketones to nitroolefins.

  2007cited by this paper
• Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple alpha,beta-unsaturated ketones.

  2007cited by this paper
• Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: beneficial effects of hydrogen bonding.

  2007cited by this paper
• Organocatalytic Asymmetric Friedel−Crafts Alkylation of Indoles with Simple α,β-Unsaturated Ketones

  2007cited by this paper
• Synthesis of Chiral Diamine Ligands Derived from Cinchona Alkaloids and Their Catalytic Performance for Asymmetric Transfer Hydrogenation

  2006cited by this paper
• Dienamine catalysis: organocatalytic asymmetric gamma-amination of alpha,beta-unsaturated aldehydes.

  2006cited by this paper
• Efficient iridium and rhodium-catalyzed asymmetric transfer hydrogenation using 9-amino(9-deoxy) cinchona alkaloids as chiral ligands

  2006cited by this paper
• Modern strategies in organic catalysis: The advent and development of iminium activation

  2006cited by this paper
• Dual-function cinchona alkaloid catalysis: catalytic asymmetric tandem conjugate addition-protonation for the direct creation of nonadjacent stereocenters.

  2006cited by this paper
• A Substrate Mimetic Approach for Influenza Neuraminidase Inhibitors.

  2005cited by this paper
• Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts.

  2005cited by this paper
• Organic azides: an exploding diversity of a unique class of compounds.

  2005cited by this paper
• Scale-Up and Safety Evaluation of a Sandmeyer Reaction

  2004cited by this paper
• The first and second cinchona rearrangement. Two fundamental transformations of alkaloid chemistry.

  2004cited by this paper
• Asymmetric Synthesis of 2-Amino-1,3-diols and D-erythro-Sphinganine.

  2004cited by this paper
• Large-scale synthesis of the anti-cancer marine natural product (+)-discodermolide. Part 1: Synthetic strategy and preparation of a common precursor

  2004cited by this paper
• Large-Scale Synthesis of the anti-Cancer Marine Natural Product (+)-Discodermolide. Part 1. Synthetic Strategy and Preparation of a Common Precursor (I).

  2004cited by this paper
• A Practical Synthesis of 6-[2-(2,5-Dimethoxyphenyl)ethyl]-4-ethylquinazoline and the Art of Removing Palladium from the Products of Pd-Catalyzed Reactions

  2003cited by this paper
• Rapid Development of an Enantioselective Synthesis of (R)-1-Hydroxy-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic Acid

  2003cited by this paper
• Safety Notables: Information from the Literature

  2003cited by this paper
• Synthesis of 9-N-cinchona alkaloid peptide hybrid derivatives: preparation and conformational study of 9-N-acylamino(9-deoxy)cinchona alkaloids.

  2003cited by this paper
• Proline-catalyzed asymmetric reactions

  2002cited by this paper
• New Strategies for Organic Catalysis: The First Highly Enantioselective Organocatalytic Diels−Alder Reaction

  2000cited by this paper
• Proline-Catalyzed Direct Asymmetric Aldol Reactions

  2000cited by this paper
• Application of the mitsunobu reaction in the field of alkaloids

  1997cited by this paper
• An Efficient Large‐Scale Synthesis of Methyl 5‐[2‐(2,5‐Dimethoxyphenyl)ethyl]‐2‐hydroxybenzoate.

  1997cited by this paper
• Dimethoxyethane as an Alternative Solvent for Schmidt Reactions. Preparation of Homochiral N-(5-Oxazolyl)oxazolidinones from N- Acetoacetyl Derivatives of Oxazolidinones.

  1996cited by this paper
• Enantioselective catalysis 98. Preparation of 9-amino(9-deoxy)cinchona alkaloids

  1995cited by this paper
• The atom economy--a search for synthetic efficiency.

  1991cited by this paper
• CONFORMATIONAL STUDY OF CINCHONA ALKALOIDS - A COMBINED NMR, MOLECULAR MECHANICS, AND X-RAY APPROACH

  1989cited by this paper
• The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products

  1981cited by this paper
• Ueber neue organische Phosphorverbindungen II. Phosphazine

  year unknowncited by this paper

• Fluoride‐Transfer Asymmetric Allylic Alkylation Enables Regiodivergent, Stereoselective Cross‐Electrophile Coupling

  2025cites this paper
• Asymmetric Total Synthesis of (+)-Karanone: An Important Aroma Compound in Fine Agarwood.

  2025cites this paper
• Protocol for the preparation of primary amine-containing catalysts on the resin

  2024cites this paper
• Synthesis and Catalytic Activity of 1,2-Benzenediamine-Derived Organocatalysts Based on (1R,2R)-Cyclohexane-1,2-Diamine

  2024cites this paper
• Enamine/Iminium-based Dual Organocatalytic Systems for Asymmetric Catalysis and Synthesis.

  2023cites this paper
• Primary amines as heterogeneous catalysts in an enantioselective [2,3]-Wittig rearrangement reaction

  2023cites this paper
• Organocatalytic Asymmetric Peroxidation of γ,δ-Unsaturated β-Keto Esters—A Novel Route to Chiral Cycloperoxides

  2023cites this paper
• Chemical Characteristics and Source-Specific Health Risks of the Volatile Organic Compounds in Urban Nanjing, China

  2022cites this paper
• Multifunctional Catalysts in the Asymmetric Mannich Reaction of Malononitrile with N-Phosphinoylimines: Coactivation by Halogen Bonding versus Hydrogen Bonding.

  2022cites this paper
• Green Chemistry Meets Asymmetric Organocatalysis: A Critical Overview on Catalysts Synthesis

  2021cites this paper
• Synthesis of C3-Symmetric Cinchona-Based Organocatalysts and Their Applications in Asymmetric Michael and Friedel-Crafts Reactions

  2021cites this paper
• Asymmetric Organocatalysis and Continuous Chemistry for an Efficient and Cost-Competitive Process to Pregabalin

  2021cites this paper
• Phytochemical Analysis and In vivo Evaluation of Individual Activity of Ethanolic Leaf Extracts of Azadirachta indica, Senna occidentalis and Momordica balsamina against Plasmodium berghei Infected Mice

  2021cites this paper
• Chiral Vicinal Diamines Derived from Mefloquine

  2021cites this paper
• Asymmetric Organocatalytic [2,3]‐Wittig Rearrangement of Cyclohexanone Derivatives

  2021cites this paper
• Industrial Relevance of Asymmetric Organocatalysis in the Preparation of Chiral Amine Derivatives

  2021cites this paper
• Supported Bifunctional Chiral Thioureas as Catalysts in the Synthesis of 3‐Amino‐2‐Oxindoles through Enantioselective aza‐Friedel‐Crafts Reaction: Application in Continuous Flow Processes

  2020cites this paper
• Synthesis of 4-azaindolines using phase transfer catalysis via an intramolecular Mannich reaction.

  2020cites this paper
• Asymmetric organocatalyzed aza-Henry reaction of hydrazones: experimental and computational studies.

  2020cites this paper
• On the nature of airborne aldehydes in a middle eastern megacity: Tehran, Iran

  2020cites this paper
• Inhibition of immunosuppressive indoleamine 2,3-dioxygenase by targeting the heme and apo-form.

  2020cites this paper
• Advances in the Mitsunobu Reaction: An Excellent Organic Protocol with Versatile Applications

  2019cites this paper
• Enantioselective organocatalytic approaches to active pharmaceutical ingredients – selected industrial examples

  2019cites this paper
• Enantioselective γ-Alkylation of α,β-Unsaturated Aldehydes Using New Cinchona-Based Primary Amine Catalyst

  2019cites this paper
• New enantiopure binaphthyl-cinchona thiosquaramides: synthesis and application for enantioselective organocatalysis

  2019cites this paper
• Adsorption of a Chiral Amine on Alginate Gel Beads and Evaluation of its Efficiency as Heterogeneous Enantioselective Catalyst

  2019cites this paper
• Organocatalytic Asymmetric Mannich Addition of 3-Fluorooxindoles to Dibenzo[b,f][1,4]oxazepines: Highly Enantioselective Construction of Tetrasubstituted C‒F Stereocenters.

  2019cites this paper
• A Silica-Supported Catalyst Containing 9-Amino-9-deoxy-9-epi -quinine and a Benzoic Acid Derivative for Stereoselective Batch and Flow Heterogeneous Reactions

  2019cites this paper
• Asymmetric vinylogous aldol addition of alkylidene oxindoles on trifluoromethyl-α,β-unsaturated ketones

  2018cites this paper
• Enantioselective Synthesis of Trifluoromethyl α,β-Unsaturated δ-Lactones via Vinylogous Aldol-Lactonization Cascade.

  2018cites this paper
• Membrane-Grafted Asymmetric Organocatalyst for an Integrated Synthesis–Separation Platform

  2018cites this paper
• Applications of Friedel–Crafts reactions in total synthesis of natural products

  2018cites this paper
• Study of the asymmetric organocatalyzed [3+2] annulation of cyclopropenone and β-keto ester

  2018cites this paper
• Targeting the Remote Control of Axial Chirality in N-(2-tert-butylphenyl)Succinimides via a Desymmetrization Strategy

  2018cites this paper
• Fluorogenic organocatalytic reactions

  2017cites this paper
• Enantio- and Diastereoselective Nitro-Mannich Reaction of α-Aryl Nitromethanes with Amidosulfones Catalyzed by Phase-Transfer Catalysts.

  2017cites this paper
• 3,5-Dinitrobenzoyl-9-amino-9-deoxy-9-epiquinine as Pirkle-Anion Exchange Hybrid-Type Chiral Selector in High-Performance Liquid Chromatography

  2017cites this paper
• Asymmetric phase-transfer catalysts bearing multiple hydrogen-bonding donors: Synthesis and application in nitro-Mannich reaction of isatin-derived N-Boc ketimines

  2017cites this paper
• Enantioselective synthesis of chiral building blocks with non-stabilized nucleophiles

  2017cites this paper
• Enantioselective Organocatalytic Diels–Alder Trapping of Photochemically Generated Hydroxy‐o‐Quinodimethanes

  2016cites this paper
• Kinetic resolution of phosphoric diester by Cinchona alkaloid derivatives provided with a guanidinium unit

  2016cites this paper
• Cinchona-Alkaloids Based Isoselenazolones: Synthesis and Their Catalytic Reactivity in Asymmetric Bromolactonization of Alkenoic Acid

  2016cites this paper
• Cinchona-Alkaloids Based Isoselenazolones: Synthesis and Their Catalytic Reactivity in Asymmetric Bromolactonization of Alkenoic Acid

  2016cites this paper
• Origins of stereoselectivity in intramolecular aldol reactions catalyzed by cinchona amines.

  2015cites this paper
• Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins

  2014cites this paper
• Asymmetric synthesis of highly functionalized tetrahydropyrans via a one-pot organocatalytic Michael/Henry/ketalization sequence.

  2014cites this paper
• Asymmetric phase-transfer catalysts bearing multiple hydrogen-bonding donors: highly efficient catalysts for enantio- and diastereoselective nitro-mannich reaction of amidosulfones.

  2014cites this paper
• Investigation of the Mitsunobu Reaction of BINOL and Cinchona Alkaloids: Inversion or Retention of Configuration?

  2014cites this paper
• One-pot biomimetic total synthesis of yuehchukene via the organocatalytic alkylation–cyclization process of a sterically encumbered α-alkyl enal

  2014cites this paper
• Enantioselective direct α-alkylation of cyclic ketones by means of photo-organocatalysis

  2014cites this paper
• Merging Gold and Organocatalysis: A Facile Asymmetric Synthesis of Annulated Pyrroles

  2014cites this paper
• How Cinchona Alkaloid-Derived Primary Amines Control Asymmetric Electrophilic Fluorination of Cyclic Ketones

  2014cites this paper
• Remote control of axial chirality: aminocatalytic desymmetrization of N-arylmaleimides via vinylogous Michael addition.

  2014cites this paper
• Control of remote stereochemistry in the synthesis of spirocyclic oxindoles: vinylogous organocascade catalysis.

  2013cites this paper
• When asymmetric aminocatalysis meets the vinylogy principle.

  2013cites this paper
• A mechanistic rationale for the 9-amino(9-deoxy)epi cinchona alkaloids catalyzed asymmetric reactions via iminium ion activation of enones.

  2013cites this paper
• Enantioselective synthesis of cis-3-fluoropiperidin-4-ol, a building block for medicinal chemistry.

  2013cites this paper