Correlating the effects of the N-substituent sizes of chiral 1,2-amino phosphinamide ligands on enantioselectivities in catalytic asymmetric Henry reaction using physical steric parameters.

No abstract is available for this paper.

• Publication year

  2014

• Venue

  Journal of Organic Chemistry

• Publication date

  2014-09-26

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/jo500982jPMID 25222868
• 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.

• Enantioselectivity switch controlled by N,N′-di- or N,N,N′,N′-tetra-substituted chiral thiophosphorodiamide ligands, structural relatives of thioureas, in catalytic additions of diethylzinc to aldehydes

  2014cited by this paper
• QSAR analysis of the catalytic asymmetric ethylation of ketone using physical steric parameters of chiral ligand substituents

  2014cited by this paper
• Interrogating selectivity in catalysis using molecular vibrations

  2014cited by this paper
• Prediction of catalyst and substrate performance in the enantioselective propargylation of aliphatic ketones by a multidimensional model of steric effects.

  2013cited by this paper
• Synergistic Effect of Achiral Quaternary Ammonium Salt on Asymmetric Additions of Diethylzinc to Aldehydes.

  2013cited by this paper
• Asymmetric catalysis: Correlating sterics in catalysis.

  2012cited by this paper
• Multidimensional steric parameters in the analysis of asymmetric catalytic reactions.

  2012cited by this paper
• Design of chiral sulfoxide-Schiff base hybrids and their application in Cu-catalyzed asymmetric Henry reactions.

  2012cited by this paper
• Constructing a quantitative correlation between N-substituent sizes of chiral ligands and enantioselectivities in asymmetric addition reactions of diethylzinc with benzaldehyde.

  2012cited by this paper
• A systematic investigation of quaternary ammonium ions as asymmetric phase-transfer catalysts. Synthesis of catalyst libraries and evaluation of catalyst activity.

  2011cited by this paper
• Predicting and optimizing asymmetric catalyst performance using the principles of experimental design and steric parameters

  2011cited by this paper
• Asymmetric Henry reaction catalyzed by a Zn–amino alcohol system

  2011cited by this paper
• Synthesis of chiral 1,3-diamines derived from cis-2-benzamidocyclohexanecarboxylic acid and their application in the Cu-catalyzed enantioselective Henry reaction.

  2011cited by this paper
• A systematic investigation of quaternary ammonium ions as asymmetric phase-transfer catalysts. Application of quantitative structure activity/selectivity relationships.

  2011cited by this paper
• Three-Dimensional Correlation of Steric and Electronic Free Energy Relationships Guides Asymmetric Propargylation

  2011cited by this paper
• Predictive modeling in homogeneous catalysis: a tutorial.

  2010cited by this paper
• Linear free-energy relationship analysis of a catalytic desymmetrization reaction of a diarylmethane-bis(phenol).

  2010cited by this paper
• Asymmetric copper(I)-catalyzed Henry reaction with an aminoindanol-derived bisoxazolidine ligand.

  2009cited by this paper
• Prediction of enantioselectivity in rhodium catalyzed hydrogenations.

  2009cited by this paper
• Examination of the role of Taft-type steric parameters in asymmetric catalysis.

  2009cited by this paper
• Brucine-derived amino alcohol catalyzed asymmetric Henry reaction: an orthogonal enantioselectivity approach.

  2009cited by this paper
• Mechanism of amido-thiourea catalyzed enantioselective imine hydrocyanation: transition state stabilization via multiple non-covalent interactions.

  2009cited by this paper
• Quantitatively correlating the effect of ligand-substituent size in asymmetric catalysis using linear free energy relationships.

  2008cited by this paper
• A library of chiral imidazoline-aminophenol ligands: discovery of an efficient reaction sphere.

  2008cited by this paper
• Catalytic asymmetric nitroaldol (Henry) reaction with a zinc-Fam catalyst.

  2008cited by this paper
• Asymmetric nitroaldol reaction catalyzed by a C2-symmetric bisoxazolidine ligand.

  2008cited by this paper
• Computational prediction of small-molecule catalysts

  2008cited by this paper
• A new copper(I)-tetrahydrosalen-catalyzed asymmetric Henry reaction and its extension to the synthesis of (S)-norphenylephrine.

  2007cited by this paper
• Asymmetric nitroaldol reaction catalyzed by a chromium(III)-salen system

  2007cited by this paper
• Highly enantioselective Henry (nitroaldol) reaction of aldehydes and alpha-ketoesters catalyzed by N,N'-dioxide-copper(I) complexes.

  2007cited by this paper
• New Quantum Mechanics-Based Three-Dimensional Molecular Descriptors for Use in QSSR Approaches: Application to Asymmetric Catalysis

  2007cited by this paper
• Chiral tetraaminophosphonium salt-mediated asymmetric direct Henry reaction.

  2007cited by this paper
• Organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane.

  2007cited by this paper
• Development of new chiral phosphine-salen type ligands and their application in the Cu(I)-catalyzed enantioselective Henry reaction

  2007cited by this paper
• Recent Advances in the Catalytic Asymmetric Nitroaldol (Henry) Reaction

  2007cited by this paper
• Catalytic asymmetric Henry reaction

  2006cited by this paper
• Calculation on enantiomeric excess of catalytic asymmetric reactions of diethylzinc addition to aldehydes with topological indices and artificial neural network

  2006cited by this paper
• Asymmetric organocatalytic Henry reaction.

  2006cited by this paper
• Diastereoselective and Enantioselective Henry (Nitroaldol) Reaction Utilizing a Guanidine‐Thiourea Bifunctional Organocatalyst

  2006cited by this paper
• Enantioselective nitroaldol (Henry) reaction using copper(II) complexes of (-)-sparteine.

  2006cited by this paper
• A priori theoretical prediction of selectivity in asymmetric catalysis: design of chiral catalysts by using quantum molecular interaction fields.

  2006cited by this paper
• Asymmetric Henry reaction catalyzed by C2-symmetric tridentate bis(oxazoline) and bis(thiazoline) complexes: metal-controlled reversal of enantioselectivity.

  2005cited by this paper
• Nanocrystalline MgO for asymmetric Henry and Michael reactions.

  2005cited by this paper
• Enantioselective henry reactions under dual Lewis acid/amine catalysis using chiral amino alcohol ligands.

  2005cited by this paper
• Unveiling reliable catalysts for the asymmetric nitroaldol (Henry) reaction.

  2004cited by this paper
• Enantioselective Henry reaction catalyzed by optically active ketoiminatocobalt complexes

  2004cited by this paper
• New β-amino alcohols with a bicyclo[3.3.0]octane scaffold in an asymmetric Henry reaction

  2004cited by this paper
• Novel chiral N4S2- and N6S3-donor macrocyclic ligands: synthesis, protonation constants, metal-ion binding and asymmetric catalysis in the Henry reaction.

  2003cited by this paper
• Computer-aided design of chiral ligands. Part 2. Functionality mapping as a method to identify stereocontrol elements for asymmetric reactions.

  2003cited by this paper
• Understanding Stereoinduction in Catalysis via Computer: New Tools for Asymmetric Synthesis

  2003cited by this paper
• Designer chiral quaternary ammonium bifluorides as an efficient catalyst for asymmetric nitroaldol reaction of silyl nitronates with aromatic aldehydes.

  2003cited by this paper
• The Importance of Being Earnest: Validation is the Absolute Essential for Successful Application and Interpretation of QSPR Models

  2003cited by this paper
• A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction.

  2003cited by this paper
• Quantitative chirality analysis of molecular subunits of bis(oxazoline)copper(II) complexes in relation to their enantioselective catalytic activity.

  2003cited by this paper
• Quantum mechanical models correlating structure with selectivity: predicting the enantioselectivity of beta-amino alcohol catalysts in aldehyde alkylation.

  2003cited by this paper
• Effect of ligand structure on the zinc-catalyzed Henry reaction. Asymmetric syntheses of (-)-denopamine and (-)-arbutamine.

  2002cited by this paper
• Beware of q2!

  2002cited by this paper
• A dinuclear Zn catalyst for the asymmetric nitroaldol (Henry) reaction.

  2002cited by this paper
• Stereocartography: a computational mapping technique that can locate regions of maximum stereoinduction around chiral catalysts.

  2002cited by this paper
• Lanthanide complexes in multifunctional asymmetric catalysis.

  2002cited by this paper
• Catalyhtic asymmetric Henry reactions--a simple approach to optically active beta-nitro alpha-hydroxy esters.

  2001cited by this paper
• Catalytic asymmetric Henry reactions—a simple approach to optically active β-nitro α-hydroxy esters

  2001cited by this paper
• Solid-Phase Synthesis of Peptidyl Trifluoromethyl Ketones

  1999cited by this paper
• Comprehensive Asymmetric Catalysis I–III

  1999cited by this paper
• re- and si-Face-Selective Nitroaldol Reactions Catalyzed by a Rigid Chiral Quaternary Ammonium Salt: A Highly Stereoselective Synthesis of the HIV Protease Inhibitor Amprenavir (Vertex 478).

  1999cited by this paper
• Steric Influences on the Selectivity in Palladium-Catalyzed Allylation

  1997cited by this paper
• Novel Transformation of Primary Nitroalkanes and Primary Alkyl Bromides to the Corresponding Carboxylic Acids.

  1997cited by this paper
• Sodium Percarbonate: A Mild Reagent for Conversion of Tosylhydrazones and Nitroalkanes to Carbonyl Compounds

  1992cited by this paper
• Basic character of rare earth metal alkoxides. Utilization in catalytic C-C bond-forming reactions and catalytic asymmetric nitroaldol reactions

  1992cited by this paper
• 1.10 – The Henry (Nitroaldol) Reaction

  1991cited by this paper

• In-silico-assisted derivatization of triarylboranes for the catalytic reductive functionalization of aniline-derived amino acids and peptides with H2

  2024cites this paper
• Data Science Guiding Analysis of Organic Reaction Mechanism and Prediction

  2024cites this paper
• Proximity effects: structural implications and quantum-chemical description. Review.

  2024cites this paper
• Mechanistic Inference from Statistical Models at Different Data-Size Regimes

  2022cites this paper
• Modern Trends in Chemical Reactions Modeling

  2021cites this paper
• Recent advances in the synthesis and applications of phosphoramides.

  2021cites this paper
• Ligand Design for Asymmetric Catalysis: Combining Mechanistic and Chemoinformatics Approaches

  2020cites this paper
• MCDCalc: Markov Chain Molecular Descriptors Calculator for Medicinal Chemistry.

  2019cites this paper
• Photothermal conversion triggered thermal asymmetric catalysis within metal nanoparticles loaded homochiral covalent organic framework

  2019cites this paper
• Quantitative Structure-Selectivity Relationships in Enantioselective Catalysis: Past, Present, and Future.

  2019cites this paper
• Steric Effect of Protonated Tertiary Amine in Primary-Tertiary Diamine Catalysis: A Double-Layered Sterimol Model.

  2019cites this paper
• Enantioselective Mannich Reaction of Glycine Iminoesters with N-Phosphinoyl Imines: A Bifunctional Approach.

  2019cites this paper
• Conformational Effects on Physical-Organic Descriptors: The Case of Sterimol Steric Parameters

  2018cites this paper
• Predictive and mechanistic multivariate linear regression models for reaction development

  2018cites this paper
• Catalytic asymmetric 1,2-Addition/Lactonization tandem reactions for the syntheses of chiral 3-Substituted phthalides using organozinc reagents

  2018cites this paper
• Enantioselective Conjugate Addition Catalyzed by a Copper Phosphoramidite Complex: Computational and Experimental Exploration of Asymmetric Induction

  2017cites this paper
• Multidimensional Correlations in Asymmetric Catalysis through Parameterization of Uncatalyzed Transition States.

  2017cites this paper
• CsB4 O6 F: A Congruent-Melting Deep-Ultraviolet Nonlinear Optical Material by Combining Superior Functional Units.

  2017cites this paper
• Chiral thiophosphoramide catalyzed asymmetric aryl transfer reactions for the synthesis of functional diarylmethanols

  2017cites this paper
• Study on the Catalytic Behavior of Bifunctional Hydrogen-Bonding Catalysts Guided by Free Energy Relationship Analysis of Steric Parameters.

  2017cites this paper
• Pd NPs-Loaded Homochiral Covalent Organic Framework for Heterogeneous Asymmetric Catalysis

  2017cites this paper
• Copper Complex of Pinene based Schiff base [CuSBADBH]2: Synthesis and its Application in Catalytic Asymmetric Nitroaldol (Henry) Reaction

  2016cites this paper
• Asymmetric Conjugate Addition of Benzofuran-2-ones to Alkyl 2-Phthalimidoacrylates: Modeling Structure-Stereoselectivity Relationships with Steric and Electronic Parameters.

  2016cites this paper
• Chiral Brønsted Acid‐Catalyzed Enantioselective α‐Amidoalkylation Reactions: A Joint Experimental and Predictive Study

  2016cites this paper
• Model Building Using Linear Free Energy Relationship Parameters-Eliminating Calibration Curves for Optical Analysis of Enantiomeric Excess.

  2016cites this paper
• Perturbation theory model of reactivity and enantioselectivity of palladium-catalyzed Heck–Heck cascade reactions

  2016cites this paper
• Novel synthesis of N-alkyl amines from tandem coupling of either methylamine or nitroalkane with aldehyde.

  2016cites this paper
• Chemo- and Enantioselective Addition and β-Hydrogen Transfer Reduction of Carbonyl Compounds with Diethylzinc Reagent in One Pot Catalyzed by a Single Chiral Organometallic Catalyst.

  2015cites this paper
• Catalytic asymmetric β-hydrogen transfer reduction of α-trifluoromethyl aromatic ketones with diethylzinc

  2015cites this paper
• One-pot protocol to synthesize N-(β-nitro)amides by tandem Henry/Ritter reaction

  2015cites this paper
• Reactivity-based dynamic covalent chemistry: reversible binding and chirality discrimination of monoalcohols.

  2015cites this paper
• Investigation on the asymmetric addition reactions between varied nonaromatic aldehydes and diethylzinc catalyzed by chiral phosphoramide and thiophosphorodiamide ligands

  2015cites this paper