Asymmetric Organocatalytic Functionalization of α,α-Disubstituted Aldehydes Through Enamine Activation

No abstract is available for this paper.

• Publication year

  2014

• Venue

  ChemInform

• Publication date

  2014-04-15

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1002/CHIN.201422270
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• An asymmetric Michael addition of α,α-disubstituted aldehydes to maleimides leading to a one-pot enantioselective synthesis of lactones catalyzed by amino acids.

  2013cited by this paper
• Chiral α-Arylethanamines: An Organocatalyst for the Enantioselective α-Amination of Branched Aldehydes

  2013cited by this paper
• Primary and secondary amine-(thio)ureas and squaramides and their applications in asymmetric organocatalysis

  2013cited by this paper
• Combining transition metal catalysis and organocatalysis--an update.

  2013cited by this paper
• Calixarene-based chiral primary amine thiourea promoted highly enantioselective asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides

  2013cited by this paper
• Enantioselective Synthesis of Succinimides by Michael Addition of Aldehydes to Maleimides Organocatalyzed by Chiral Primary Amine‐Guanidines

  2013cited by this paper
• Direct asymmetric α-allylation of α-branched aldehydes by two catalytic systems with an achiral Pd complex and a chiral primary α-amino acid.

  2013cited by this paper
• Enantio- and Diastereodivergent Dual Catalysis: α-Allylation of Branched Aldehydes

  2013cited by this paper
• Synthesis of the atropurpuran A-ring via an organocatalytic asymmetric intramolecular Michael addition

  2013cited by this paper
• β-tert-Butyl aspartate as an organocatalyst for the asymmetric α-amination of α,α-disubstituted aldehydes

  2013cited by this paper
• The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide.

  2013cited by this paper
• Curtin-Hammett paradigm for stereocontrol in organocatalysis by diarylprolinol ether catalysts.

  2012cited by this paper
• Organocatalytic asymmetric α-benzoyloxylation of α-branched aldehydes and enals: a useful approach to oxygenated quaternary stereocenters

  2012cited by this paper
• Organocatalytic Enantioselective α‐Alkylation of Aldehydes

  2012cited by this paper
• Relative tendency of carbonyl compounds to form enamines.

  2012cited by this paper
• Isoleucine-catalyzed direct asymmetric aldol addition of enolizable aldehydes.

  2012cited by this paper
• Enantioselective synthesis of gabapentin analogues via organocatalytic asymmetric Michael addition of α-branched aldehydes to β-nitroacrylates.

  2012cited by this paper
• Mechanism and stereoselectivity of a dual amino-catalyzed robinson annulation: rare duumvirate stereocontrol.

  2012cited by this paper
• Histidine-catalyzed asymmetric aldol addition of enolizable aldehydes: insights into its mechanism.

  2012cited by this paper
• Copper(I)-amine metallo-organocatalyzed synthesis of carbo- and heterocyclic systems.

  2012cited by this paper
• Asymmetric Organocatalysis 1: Lewis Base and Acid Catalysts

  2012cited by this paper
• Noncovalent bifunctional organocatalysts: powerful tools for contiguous quaternary-tertiary stereogenic carbon formation, scope, and origin of enantioselectivity.

  2012cited by this paper
• Proline sulphonamide-catalysed Yamada-Otani condensation: reaction development, substrate scope and scaffold reactivity.

  2012cited by this paper
• A general stereoselective enamine mediated alkylation of α-substituted aldehydes.

  2012cited by this paper
• Fluorinated organocatalysts for the enantioselective epoxidation of enals: molecular preorganisation by the fluorine-iminium ion gauche effect.

  2012cited by this paper
• Stereoselectivities of histidine-catalyzed asymmetric aldol additions and contrasts with proline catalysis: a quantum mechanical analysis.

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

  2012cited by this paper
• Highly Efficient Asymmetric Conjugate Additions of Aldehydes with Vinyl Sulfones Using a Sulfonamide Organocatalyst

  2012cited by this paper
• Enantioselective Michael addition of α,α-disubstituted aldehydes to maleimides organocatalyzed by chiral primary amine-guanidines

  2012cited by this paper
• Enantioselective organocatalytic one-pot amination/aza-Michael/aldol condensation reaction sequence: synthesis of 3-pyrrolines with a quaternary stereocenter.

  2012cited by this paper
• Primary amine/CSA ion pair: a powerful catalytic system for the asymmetric enamine catalysis.

  2011cited by this paper
• Mechanisms in aminocatalysis.

  2011cited by this paper
• Catalytic asymmetric aziridination of α,β-unsaturated aldehydes.

  2011cited by this paper
• Direct asymmetric N-specific reaction of nitrosobenzene with aldehydes catalyzed by a chiral primary amine-based organocatalyst.

  2011cited by this paper
• Chiral primary amine catalyzed enantioselective protonation via an enamine intermediate.

  2011cited by this paper
• Practical access to highly enantioenriched quaternary carbon Michael adducts using simple organocatalysts.

  2011cited by this paper
• Direct asymmetric α-allylation of aldehydes with simple allylic alcohols enabled by the concerted action of three different catalysts.

  2011cited by this paper
• Asymmetric organocatalytic Michael-α-amination sequence for the construction of a quaternary stereocenter.

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

  2011cited by this paper
• Asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides using a primary amine thiourea organocatalyst

  2011cited by this paper
• Primary amine catalyzed electrophilic amination of α,α-disubstituted aldehydes

  2011cited by this paper
• Direct Organocatalytic α-Sulfenylationof Aldehydes and Ketones with Tetramethylthiuram Disulfide

  2011cited by this paper
• Organocatalyzed Aziridination of α‐Branched Enals: Enantioselective Synthesis of Aziridines with a Quaternary Stereocenter.

  2011cited by this paper
• Enantioselective α-amination of branched aldehydes promoted by simple chiral primary amino acids.

  2011cited by this paper
• Asymmetric Michael additions of aldehydes to maleimides using a recyclable fluorous thiourea organocatalyst

  2011cited by this paper
• A highly efficient large-scale asymmetric Michael addition of isobutyraldehyde to maleimides promoted by a novel multifunctional thiourea

  2011cited by this paper
• Enantioselective organocatalytic formal allylation of α-branched aldehydes.

  2011cited by this paper
• Highly enantioselective Michael addition of aldehydes to nitroolefins catalyzed by primary amine thiourea organocatalysts

  2010cited by this paper
• Organocatalyzed cyclopropanation of alpha-substituted alpha,beta-unsaturated aldehydes: enantioselective synthesis of cyclopropanes bearing a chiral quaternary center.

  2010cited by this paper
• Asymmetric Michael addition of aldehydes to nitroalkenes using a primary amino acid lithium salt.

  2010cited by this paper
• Organocatalytic enantioselective aziridination of α-substituted α,β-unsaturated aldehydes: Asymmetric synthesis of terminal aziridines

  2010cited by this paper
• Highly asymmetric Michael additions of α,α-disubstituted aldehydes to β-nitroalkenes promoted by chiral pyrrolidine–thiourea bifunctional catalysts

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

  2010cited by this paper
• Effective construction of quaternary stereocenters by highly enantioselective α-amination of branched aldehydes.

  2010cited by this paper
• Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to beta-nitroalkenes.

  2010cited by this paper
• A simple primary amine thiourea catalyzed highly enantioselective conjugate addition of alpha,alpha-disubstituted aldehydes to maleimides.

  2010cited by this paper
• Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency.

  2010cited by this paper
• Asymmetric addition of alpha-hetero-disubstituted aldehydes to vinyl sulfones; formation of highly functionalized tetrasubstituted carbon centres.

  2010cited by this paper
• Asymmetric epoxidation of α-substituted acroleins catalyzed by diphenylprolinol silyl ether.

  2010cited by this paper
• Combined InCl3- and amine-catalyzed intramolecular addition of alpha-disubstituted aldehydes onto unactivated alkynes.

  2010cited by this paper
• Enantioselective synthesis of polysubstituted cyclopentanones by organocatalytic double Michael addition reactions.

  2010cited by this paper
• Chiral primary amine mediated conjugate addition of branched aldehydes to vinyl sulfone: asymmetric generation of quaternary carbon centers.

  2010cited by this paper
• Chiral primary amine thiourea promoted highly enantioselective Michael reactions of isobutylaldehyde with maleimides

  2010cited by this paper
• Design of structurally rigid trans-diamine-based Tf-amide organocatalysts with a dihydroanthracene framework for asymmetric conjugate additions of heterosubstituted aldehydes to vinyl sulfones.

  2010cited by this paper
• A highly efficient asymmetric Michael addition of α,α-disubstituted aldehydes to maleimides catalyzed by primary amine thiourea salt.

  2010cited by this paper
• Asymmetric synthesis of deuterated and fluorinated aromatic α,α-disubstituted amino acid derivatives

  2010cited by this paper
• Chiral Primary Amine Catalyzed Asymmetric Epoxidation of α‐Substituted Acroleins

  2010cited by this paper
• Chemzymes: a new class of structurally rigid tricyclic amphibian organocatalyst inspired by natural product.

  2010cited by this paper
• Aminal–Pyrrolidine Organocatalysts – Highly Efficient and Modular Catalysts for α‐Functionalization of Carbonyl Compounds

  2010cited by this paper
• Enantioselective catalytic alpha-alkylation of aldehydes via an SN1 pathway.

  2010cited by this paper
• A new powerful strategy for the organocatalytic asymmetric construction of a quaternary carbon stereogenic center.

  2010cited by this paper
• Highly Efficient and Practical Pyrrolidine–Camphor‐Derived Organocatalysts for the Direct α‐Amination of Aldehydes

  2010cited by this paper
• Rapid, general access to chiral beta-fluoroamines and beta,beta-difluoroamines via organocatalysis.

  2009cited by this paper
• Highly enantioselective conjugate addition of aldehydes to nitroolefins catalyzed by chiral bifunctional sulfamides.

  2009cited by this paper
• Synergic asymmetric organocatalysis (SAOc) of Cinchona alkaloids and secondary amines in the synthesis of bicyclo[2.2.2]octan-2-ones.

  2009cited by this paper
• Organocatalysis--after the gold rush.

  2009cited by this paper
• Asymmetric conjugate addition of carbonyl compounds to nitroalkenes catalyzed by chiral bifunctional thioureas

  2009cited by this paper
• Organocatalytic formation of quaternary stereocenters

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

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

  2009cited by this paper
• Asymmetric histidine-catalyzed cross-aldol reactions of enolizable aldehydes: access to defined configured quaternary stereogenic centers.

  2009cited by this paper
• Towards an asymmetric synthesis of the bacterial peptide deformylase (PDF) inhibitor fumimycin.

  2009cited by this paper
• Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging Michael acceptors.

  2009cited by this paper
• 3-trifluoromethanesulfonamido-pyrrolidine: a general organocatalyst for anti-selective mannich reactions.

  2008cited by this paper
• Primary amino acid lithium salt as a catalyst for asymmetric Michael addition of isobutyraldehyde with beta-nitroalkenes.

  2008cited by this paper
• Highly efficient catalytic system for enantioselective Michael addition of aldehydes to nitroalkenes in water.

  2008cited by this paper
• Enantioselective organocatalytic conjugate addition of aldehydes to nitrodienes.

  2008cited by this paper
• Efficient synthesis of gamma-lactams by a tandem reductive amination/lactamization sequence.

  2008cited by this paper
• Organocatalytic asymmetric domino reactions: a cascade consisting of a Michael addition and an aldehyde alpha-alkylation.

  2008cited by this paper
• Thermal Effects in the Organocatalytic Asymmetric α‐Amination of Disubstituted Aldehydes with Azodicarboxylates: A High‐Temperature Organocatalysis

  2008cited by this paper
• Asymmetric Michael Addition Reactions of Aldehydes with Nitrostyrenes Catalyzed by Functionalized Chiral Ionic Liquids.

  2008cited by this paper
• Quaternary stereogenic carbon atoms in complex molecules by an asymmetric, organocatalytic, triple-cascade reaction.

  2008cited by this paper
• Stereoselective synthesis of alpha,alpha-chlorofluoro carbonyl compounds leading to the construction of fluorinated chiral quaternary carbon centers.

  2008cited by this paper
• Direct carbocyclization of aldehydes with alkynes: combining gold catalysis with aminocatalysis.

  2008cited by this paper
• The Proline‐Catalyzed Asymmetric Amination of Branched Aldehydes

  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 enantioselective conjugate addition of aldehydes to maleimides.

  2007cited by this paper
• Highly Asymmetric Michael Addition to α,β‐Unsaturated Ketones Catalyzed by 9‐Amino‐9‐deoxyepiquinine

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

  2007cited by this paper
• Direct Asymmetric α‐Sulfamidation of α‐Branched Aldehydes: A Novel Approach to Enamine Catalysis

  2006cited by this paper

• Primary Amine-Catalyzed Enantioselective Fluorination of α-Branched Aldehydes with Low Catalyst Loadings.

  2025cites this paper
• An Enantioselective Nucleophilic Aromatic tele-Substitution.

  2025cites this paper
• Cinchona Organocatalyzed Enantioselective Amination for Quaternized Serines as Tertiary Amides

  2024cites this paper
• Catalytic Asymmetric Synthesis of Vicinal Quaternary Stereocenters Enabled by Alkylation of α,α-Disubstituted Aldehydes with 3-Bromooxindoles.

  2024cites this paper
• Highly selective C3-sulfenylation and C3-selenylation of 3-iodo-5-arylpyrazolo[1,5-a]pyrimidin-7-amine in water

  2023cites this paper
• Catalytic Asymmetric α-Functionalization of α-Branched Aldehydes

  2023influential citation
• Catalytic Enantioselective Alkylation of Aldehydes with 3-Bromooxindoles.

  2023cites this paper
• Asymmetric Dual Enamine Catalysis/Hydrogen Bonding Activation

  2023cites this paper
• C4-Sulfenylation of 4-iodine-1H-pyrazole-5-amine with arylsulfonyl hydrazide in water

  2022cites this paper
• syn ‐Selective Michael Reaction of α‐Branched Aryl Acetaldehydes with Nitroolefins Promoted by Squaric Amino Acid Derived Bifunctional Brønsted Bases

  2021cites this paper
• Asymmetric Supramolecular Organocatalysis: The Fourth Pillar of Catalysis

  2021cites this paper
• TBAI-mediated sulfenylation of arenes with arylsulfonyl hydrazides in DPDME

  2020cites this paper
• Improvement of primary-amine-catalyzed asymmetric α-benzoyloxylation of α-branched enals by a synergistic effect of water and sulfonic acids

  2020cites this paper
• Asymmetric Michael Addition of Isobutyraldehyde to Nitroolefins Using an α,α-Diphenyl-(S)-prolinol-Derived Chiral Diamine Catalyst

  2020cites this paper
• Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts.

  2020cites this paper
• Asymmetric Electrophilic Amination and Hydrazination of Acyclic α-Branched Ketones for the Formation of α-Tertiary Amines and Hydrazines

  2019cites this paper
• Asymmetric Cycloaddition Reactions of Oxindole α-Keto Esters via Cascade Dienamine-Enamine and Trienamine Strategies

  2019cites this paper
• l-Prolinal Dithioacetal: A Highly Effective Organocatalyst for the Direct Nitro-Michael Addition to Selected Cyclic and Aromatic Ketones

  2019cites this paper
• Diastereoselective α-Amination of N- tert-Butanesulfinyl Imidates Using N-Aryl- N-diphenylphosphinyldiazenes.

  2019cites this paper
• A Novel Catalyst-Free Synthesis of 2,2-Diaryl Enamides from Stilbenes via a Nitrene Transfer Reaction

  2019cites this paper
• Synthesis of the diarylindolizidine alkaloid (+)-Fistulopsine B: Application of an organocatalytic Michael addition reaction

  2018cites this paper
• Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters

  2018cites this paper
• α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation.

  2018cites this paper
• Metal-free visible-light synthesis of quaternary α-perfluoroalkyl aldehydes via an enamine intermediate.

  2018cites this paper
• Aminocatalytic Privileged Diversity‐Oriented Synthesis (ApDOS): An Efficient Strategy to Populate Relevant Chemical Spaces

  2018cites this paper
• Branched aldehydes as linchpins for the enantioselective and stereodivergent synthesis of 1,3-aminoalcohols featuring a quaternary stereocentre

  2018cites this paper
• An organocatalytic enantioselective direct α-heteroarylation of aldehydes with isoquinoline N-oxides.

  2018cites this paper
• Iodine-mediated sulfenylation of 4-hydroxycoumarins with sulfonyl hydrazides under aqueous conditions

  2018cites this paper
• Quaternized α,α'-Amino Acids via Curtius Rearrangement of Substituted Malonate-Imidazolidinones.

  2017cites this paper
• Enantioselective organocatalytic α-sulfamidation of aldehydes using sulfonyl azides

  2017cites this paper
• Organocatalytic enantioselective conjugate addition of aldehydes to maleimides in deep eutectic solvents

  2017cites this paper
• Sulfenylation of C–H Bonds for C–S Bond Formation under Metal‐Free Conditions

  2017cites this paper
• Prolinal dithioacetals: Highly efficient organocatalysts for the direct nitro-Michael additions in both organic and aqueous media

  2017cites this paper
• Asymmetric Supramolecular Organocatalysis: A Complementary Upgrade to Organocatalysis

  2017cites this paper
• Chemoselective room temperature E1cB N-N cleavage of oxazolidinone hydrazides from enantioselective aldehyde α-hydrazination: synthesis of (+)-1,4-dideoxyallonojirimycin.

  2016cites this paper
• Old tricks, new dogs: organocatalytic dienamine activation of α,β-unsaturated aldehydes

  2016cites this paper
• Dual Catalysis Using Boronic Acid and Chiral Amine: Acyclic Quaternary Carbons via Enantioselective Alkylation of Branched Aldehydes with Allylic Alcohols.

  2016cites this paper
• Novel bifunctional l-prolinamide derivatives as highly efficient organocatalysts for asymmetric nitro-Michael reactions

  2016cites this paper
• The Organocatalytic α‐Fluorination of Chiral γ‐Nitroaldehydes: the Challenge of Facing the Construction of a Quaternary Fluorinated Stereocenter

  2016cites this paper
• Proline Sulfonamide‐Catalyzed, ­Domino Process for Asymmetric Synthesis of Amino‐ and Hydroxy‐Substituted Bicyclo[2.2.2]octanes

  2016cites this paper
• Bifunctional primary amine 2-aminobenzimidazole organocatalyst anchored to trans-cyclohexane-1,2-diamine in enantioselective conjugate additions of aldehydes

  2016cites this paper
• Diastereoselective synthesis of furanose and pyranose substituted glycine and alanine derivatives via proline-catalyzed asymmetric α-amination of aldehydes.

  2016cites this paper
• Asymmetric dual catalysis via fragmentation of a single rhodium precursor complex.

  2016cites this paper
• Open-close: an alternative strategy to α-functionalization of lactone via enamine catalysis in one pot under mild conditions.

  2015cites this paper
• Solvent‐Induced Reversal of Enantioselectivity in the Synthesis of Succinimides by the Addition of Aldehydes to Maleimides Catalysed by Carbamate‐Monoprotected 1,2‐Diamines

  2015cites this paper
• A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes.

  2015cites this paper
• Divergent synthesis of various iminocyclitols from D-ribose.

  2015cites this paper
• Importance of the Electron Correlation and Dispersion Corrections in Calculations Involving Enamines, Hemiaminals, and Aminals. Comparison of B3LYP, M06-2X, MP2, and CCSD Results with Experimental Data.

  2015cites this paper
• Transfer of 1-alkenyl groups between secondary amines. relative stability and reactivity of enamines from popular organocatalysts.

  2014cites this paper
• Solvent-dependent enantioswitching in the Michael addition of α,α-disubstituted aldehydes to maleimides organocatalyzed by mono-N-Boc-protected cyclohexa-1,2-diamines

  2014cites this paper
• Selecting reactions and reactants using a switchable rotaxane organocatalyst with two different active sites† †Electronic supplementary information (ESI) available: Synthetic procedures and characterisation data. See DOI: 10.1039/c4sc03279a Click here for additional data file.

  2014cites this paper
• Synthesis of bis-α-amino acids through proline catalyzed asymmetric α-amination of higher homologs of Garner's aldehyde

  2014cites this paper
• Exploring the activation modes of a rotaxane-based switchable organocatalyst.

  2014cites this paper