Construction of Optically Active Quaternary Propargyl Amines by Highly Enantioselective Zinc/BINOL-Catalyzed Alkynylation of Ketoimines.

No abstract is available for this paper.

• Publication year

  2013

• Venue

  Chemistry

• Publication date

  2013-09-02

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/chem.201301479PMID 23857799
• 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.

• Direct catalytic asymmetric alkynylation of ketoimines.

  2013cited by this paper
• Enantioselective organocatalytic synthesis of quaternary α-amino acids bearing a CF3 moiety.

  2011cited by this paper
• Catalytic asymmetric alkynylation of C1-substituted C,N-cyclic azomethine imines by Cu(I)/chiral Brønsted acid co-catalyst.

  2011cited by this paper
• Highly diastereoselective synthesis of quaternary α-trifluoromethyl α-amino acids by addition of benzylzinc reagents to chiral imines of trifluoropyruvate

  2011cited by this paper
• Highly enantioselective zinc/BINOL-catalyzed alkynylation of α-ketoimine ester: a new entry to optically active quaternary α-CF3 α-amino acids.

  2011cited by this paper
• Organocatalytic Enantioselective Strecker Synthesis of α-Quaternary α-Trifluoromethyl Amino Acids

  2010cited by this paper
• Asymmetrische Alkinylierung von Iminen durch Kooperation von Wasserstoffbrücken und Metallkatalyse

  2010cited by this paper
• Copper-catalyzed enantioselective three-component synthesis of optically active propargylamines from aldehydes, amines, and aliphatic alkynes.

  2010cited by this paper
• Highly diastereoselective synthesis of quaternary α-trifluoromethyl α-amino acids from chiral imines of trifluoropyruvate.

  2010cited by this paper
• Asymmetric alkynylation of imines by cooperative hydrogen bonding and metal catalysis.

  2010cited by this paper
• Ag-catalyzed diastereo- and enantioselective vinylogous Mannich reactions of alpha-ketoimine esters. Development of a method and investigation of its mechanism.

  2009cited by this paper
• Organocatalytic formation of quaternary stereocenters

  2009cited by this paper
• Iodocyclization of chiral CF3-allylmorpholinones: a versatile strategy for the synthesis of enantiopure alpha-Tfm-prolines and alpha-Tfm-dihydroxyprolines.

  2009cited by this paper
• Nitrogen-Containing OrganofluorineDerivatives: An Overview

  2009cited by this paper
• The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

  2009cited by this paper
• Hydrogen-bonding asymmetric metal catalysis with alpha-amino acids: a simple and tunable approach to high enantioinduction.

  2009cited by this paper
• Catalytic asymmetric alkylations of ketoimines. Enantioselective synthesis of N-substituted quaternary carbon stereogenic centers by Zr-catalyzed additions of dialkylzinc reagents to aryl-, alkyl-, and trifluoroalkyl-substituted ketoimines.

  2008cited by this paper
• Asymmetric synthesis of tertiary alcohols and alpha-tertiary amines via Cu-catalyzed C-C bond formation to ketones and ketimines.

  2008cited by this paper
• Synthetic strategies to alpha-trifluoromethyl and alpha-difluoromethyl substituted alpha-amino acids.

  2008cited by this paper
• Highly enantioselective zinc/binol-catalyzed alkynylation of N-sulfonyl aldimines.

  2008cited by this paper
• Duale Katalyse: eine kombinierte enantioselektive Brønsted‐Säure‐ und metallkatalysierte Reaktion – Metallkatalyse mit chiralem Gegenion

  2007cited by this paper
• Dual catalysis: a combined enantioselective Brønsted acid and metal-catalyzed reaction--metal catalysis with chiral counterions.

  2007cited by this paper
• Dimethylzinc-mediated, enantioselective synthesis of propargylic amines.

  2007cited by this paper
• En route to an efficient catalytic asymmetric synthesis of AS-3201.

  2007cited by this paper
• Asymmetric activation of tropos 2,2'-biphenol with cinchonine generates an effective catalyst for the asymmetric strecker reaction of N-tosyl-protected aldimines and ketoimines.

  2007cited by this paper
• Catalytic enantioselective Mannich-type reactions of ketoimines.

  2007cited by this paper
• Asymmetric catalysis for the construction of quaternary carbon centres: nucleophilic addition on ketones and ketimines.

  2007cited by this paper
• Catalytic enantioselective allylation of ketoimines.

  2006cited by this paper
• How C(alpha)-Fluoroalkyl amino acids and peptides interact with enzymes: studies concerning the influence on proteolytic stability, enzymatic resolution and peptide coupling.

  2006cited by this paper
• Catalytic asymmetric synthesis of alpha,alpha,alpha-trifluoromethylamines by the copper-catalyzed nucleophilic addition of diorganozinc reagents to imines.

  2006cited by this paper
• Enantioselective one-pot three-component synthesis of propargylamines.

  2006cited by this paper
• Straightforward synthesis of (S)- and (R)-alpha-trifluoromethyl proline from chiral oxazolidines derived from ethyl trifluoropyruvate.

  2006cited by this paper
• Asymmetric synthesis of propargylamides via 3,3'-disubstituted binaphthol-modified alkynylboronates.

  2006cited by this paper
• A synthesis of (+)-saxitoxin.

  2006cited by this paper
• Incorporation of the unusual C(alpha)-fluoroalkylamino acids into cyclopeptides: synthesis of arginine-glycine-aspartate (RGD) analogues and study of their conformational and biological behavior.

  2006cited by this paper
• Direct addition of alkynes to imines and related C=N electrophiles: A convenient access to propargylamines.

  2006cited by this paper
• Catalytic Asymmetric Synthesis of α,α,α-Trifluoromethylamines by the Copper-Catalyzed Nucleophilic Addition of Diorganozinc Reagents to Imines

  2006cited by this paper
• Catalytic asymmetric alkynylation of alpha-imino ester: a versatile approach to optically active unnatural alpha-amino acid derivatives.

  2005cited by this paper
• Experimental and computational studies of ring inversion of 1,4-benzodiazepin-2-ones: implications for memory of chirality transformations.

  2005cited by this paper
• Catalytic asymmetric alkynylation of α-imino ester: A versatile approach to optically active unnatural α-amino acid derivatives

  2005cited by this paper
• Stereoselective synthesis of d-desosamine and related glycals via tungsten-catalyzed alkynol cycloisomerization.

  2004cited by this paper
• Readily available biaryl P,N ligands for asymmetric catalysis.

  2004cited by this paper
• Highly enantioselective phenylacetylene additions to ketones catalyzed by (S)-BINOL-Ti complex.

  2004cited by this paper
• Trifluoromethyl group: an effective xenobiotic function for peptide backbone modification

  2004cited by this paper
• Acetylenes in Catalysis: Enantioselective Additions to Carbonyl Groups and Imines and Applications Beyond

  2004cited by this paper
• Direct organocatalytic enantioselective mannich reactions of ketimines: an approach to optically active quaternary alpha-amino acid derivatives.

  2004cited by this paper
• Highly enantioselective construction of a chiral tertiary carbon center by alkynylation of a cyclic N-acyl ketimine: an efficient preparation of HIV therapeutics.

  2004cited by this paper
• Synthesis of fluorinated amino acids

  2004cited by this paper
• Cu(I)-catalyzed direct addition and asymmetric addition of terminal alkynes to imines.

  2004cited by this paper
• Stereocontrolled total synthesis of (+)-streptazolin by a palladium-catalyzed reductive diyne cyclization.

  2004cited by this paper
• Enantioselective synthesis of "quaternary" 1,4-benzodiazepin-2-one scaffolds via memory of chirality.

  2003cited by this paper
• Enantioselective alkynylation of aromatic ketones catalyzed by chiral camphorsulfonamide ligands.

  2003cited by this paper
• Catalytic enantioselective Strecker reaction of ketoimines.

  2003cited by this paper
• Eine enantioselektive, Kupfer(I)‐katalysierte Drei‐Komponenten‐Reaktion zur Synthese von Propargylaminen

  2003cited by this paper
• Enantioselective, copper(I)-catalyzed three-component reaction for the preparation of propargylamines.

  2003cited by this paper
• Enantioselective direct-addition of terminal alkynes to imines catalyzed by copper(I)pybox complex in water and in toluene.

  2002cited by this paper
• Structure-based analysis and optimization of a highly enantioselective catalyst for the strecker reaction.

  2002cited by this paper
• Design in topographical space of peptide and peptidomimetic ligands that affect behavior. A chemist's glimpse at the mind--body problem.

  2001cited by this paper
• Efficient synthesis of an optically pure β-bromo-β,β-difluoroalanine derivative, a general precursor for β,β-difluoroamino acids

  2001cited by this paper
• Catalytic asymmetric organozinc additions to carbonyl compounds.

  2001cited by this paper
• Enantioselective construction of quaternary stereocenter through a Reissert-type reaction catalyzed by an electronically tuned bifunctional catalyst: efficient synthesis of various biologically significant compounds.

  2001cited by this paper
• An improved synthesis of chiral alpha-(4-bromobenzyl)alanine ethyl ester and its application to the synthesis of LFA-1 antagonist BIRT-377.

  2001cited by this paper
• Novel conformationally constrained tropane analogues by 6-endo-trig radical cyclization and stille coupling - switch of activity toward the serotonin and/or norepinephrine transporter.

  2000cited by this paper
• First synthesis of 3,3-difluoroserine and cysteine derivatives via Mg(0)-promoted selective CF bond cleavage of trifluoromethylimines

  2000cited by this paper
• An efficient chiral moderator prepared from inexpensive (+)-3-carene: synthesis of the HIV-1 non-nucleoside reverse transcriptase inhibitor DPC 963.

  2000cited by this paper
• Stereochemical control of peptide folding.

  1999cited by this paper
• Methods for the synthesis of gem-difluoromethylene compounds

  1996cited by this paper
• Lithium Alkoxides of Cinchona Alkaloids as Chiral Controllers for Enantioselective Acetylide Addition to Cyclic N-Acyl Ketimines

  1995cited by this paper
• New Amino Acids for the Topographical Control of Peptide Conformation: Synthesis of All the Isomers of .alpha.,.beta.-Dimethylphenylalanine and .alpha.,.beta.-Dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid of High Optical Purity

  1994cited by this paper
• PEPTIDMIMETICA FUR REZEPTORLIGANDEN : ENTDECKUNG, ENTWICKLUNG UND MEDIZINISCHE PERSPEKTIVEN

  1993cited by this paper
• Peptidomimetics for Receptor Ligands—Discovery, Development, and Medical Perspectives

  1993cited by this paper
• Homologation of trifluoroacetimidoyl iodides by palladium-catalyzed carbonylation. An approach to α-amino perfluoroalkanoic acids.

  1992cited by this paper
• Monofluoro- and difluoro-methylenebisphosphonic acids: isopolar analogues of pyrophosphoric acid

  1981cited by this paper

• An Attractive and Efficient Method for Preparation of Propargyl Amines: Presentation of a Novel Magnetically Reusable Manganese Nanocatalyst for C-N Bond Formation

  2024cites this paper
• Asymmetric α-Fluoroalkyl-α-Amino Acids: Recent Advances in Their Synthesis and Applications

  2024cites this paper
• Redox-Active α-Amino-CF3 Reagents: Developing and Applications in Ni-Catalyzed Reductive Cross-Coupling.

  2024cites this paper
• Catalyst-Tuned Regiodivergent and Enantioselective Formal Hydroaminations of Acryamides to α-Tertiary-α-Aminolactam and β-Aminoamide Derivatives.

  2023cites this paper
• A new binuclear Ni(II) complex, an effective A3-coupling catalyst in solvent-free condition

  2023cites this paper
• Advances in Mannich‐type Reactions Based on the Classification of Compounds with Activated α‐H

  2023cites this paper
• Copper(I)-BOX Catalyzed Asymmetric 3-Component Reaction for the Synthesis of Trifluoromethylated Propargylic Ethers and Anilines.

  2023cites this paper
• Accessing unnatural α-amino acids with tetrasubstituted stereogenic centers via catalytic enantioselective reactions of ketimine-type α-iminoesters/α-iminoamides.

  2023cites this paper
• Dearomative Insertion of Fluoroalkyl Carbenes into Azoles Leading to Fluoroalkyl Heterocycles with a Quaternary Center.

  2023cites this paper
• Fluorine-Containing Prolines: Synthetic Strategies, Applications, and Opportunities.

  2022cites this paper
• Modern Approaches to Synthetic Design of Chiral α-Tertiary Amines Based on Trifluoromethylcontaining Ketimines: A Review

  2022cites this paper
• Visible-Light-Mediated Carbonyl Alkylative Amination to All-Alkyl α-Tertiary Amino Acid Derivatives.

  2021cites this paper
• Cu(I)-Catalyzed gem-Aminoalkynylation of Diazo Compounds: Synthesis of Fluorinated Propargylic Amines.

  2021cites this paper
• Biradical o-iminobenzosemiquinonato(1−) complexes of nickel(ii): catalytic activity in three-component coupling of aldehydes, amines and alkynes

  2021cites this paper
• Divergent synthesis of functionalized dihydropyridines and pyrroles via metal-free one-pot domino reactions of a gem-disubstituted propargyl amine and an alkynyl sulfone

  2021cites this paper
• Kinetic Resolution of α-Tertiary Propargylic Amines through Asymmetric Remote Aminations of Anilines

  2021cites this paper
• Synthesis of enantiopure α-Tfm-proline and α-Tfm-pipecolic acid from oxazolo-pyrrolidines and -piperidines.

  2021cites this paper
• Recent Progress on Catalytic Addition Reactions to N-Unsubstituted Imines

  2020cites this paper
• Strategies for the Catalytic Enantioselective Synthesis of α-Trifluoromethyl Amines.

  2020cites this paper
• Recent Advances in Catalytic Enantioselective Synthesis of Fluorinated α‐ and β‐Amino Acids

  2020cites this paper
• Polarity effects in 4-fluoro- and 4-(trifluoromethyl)prolines

  2020cites this paper
• Catalytic Asymmetric Mannich‐Type Reaction of Malononitrile with N‐Boc α‐Ketiminoesters Using Chiral Organic Base Catalyst with Halogen Bond Donor Functionality

  2020cites this paper
• Copper-based catalysts derived from salen-type ligands: synthesis of 5-substituted-1H-tetrazoles via [3+2] cycloaddition and propargylamines via A3-coupling reactions

  2020cites this paper
• Zn-Catalyzed Multicomponent KA2 Coupling: One-Pot Assembly of Propargylamines Bearing Tetrasubstituted Carbon Centers

  2019cites this paper
• Enantiodivergence by minimal modification of an acyclic chiral secondary aminocatalyst

  2019cites this paper
• Copper-Catalyzed Borylative Multicomponent Synthesis of Quaternary α-Amino Esters

  2019cites this paper
• Enantioselective Catalytic Allylation of Acyclic Ketiminoesters: Synthesis of α-Fully-Substituted Amino Esters.

  2019cites this paper
• Synthesis of α-Trifluoromethylamines by Cu-Catalyzed Regio- and Enantioselective Hydroamination of 1-Trifluoromethylalkenes.

  2019cites this paper
• Synthesis of α-CF3-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors.

  2019cites this paper
• The Catalytic Asymmetric Construction of Trifluoromethylated Quaternary Carbon-Containing Thiochromans

  2019cites this paper
• Direct α-Imination of N-Acyl Pyrazoles with Nitrosoarenes.

  2019cites this paper
• Enantioselective Friedel-Crafts Alkylation Reaction of Heteroarenes with N-Unprotected Trifluoromethyl Ketimines by Means of Chiral Phosphoric Acid.

  2019cites this paper
• Comparative effects of trifluoromethyl- and methyl-group substitutions in proline

  2018cites this paper
• Asymmetric Synthesis of Cyclic Fluorinated Amino Acids

  2018cites this paper
• Synthesis of Optically Active α-Trifluoromethylamines by Rearrangement of β-Amino-α-trifluoromethyl Alcohols.

  2018cites this paper
• Organocatalytic Asymmetric Reduction of Fluorinated Alkynyl Ketimines.

  2018cites this paper
• Successive addition of two different Grignard reagents to nitriles: access to α,α-disubstituted propargylamine derivatives.

  2018cites this paper
• From Cyclic Ketimines to α‐Substituted Cyclic Amino Acids and their Derivatives: Influence of Ring Size and Substituents on Stability and Reactivity of Cyclic Aminonitriles

  2018cites this paper
• Base-catalyzed cascade 1,6-sulfur-Michael/Henry reaction of trifluoromethyl-substituted styrylisoxazoles: Diastereoselective synthesis of tetrahydrothiophenes with a trifluoromethylated quaternary center

  2018cites this paper
• Enantioselective synthesis of α-perfluoroalkylated prolines, their 6,7-membered homologues and derivatives.

  2018cites this paper
• Diastereoselective Trifluoromethylation of Chiral α,β-UnsaturatedN-tert-Butanesulfinyl Ketimines with Ruppert-Prakash Reagent: Asymmetric Synthesis of α-Tertiary Trifluoromethyl Allylic Amines

  2018cites this paper
• A diastereoselective Mannich reaction of α-fluoroketones with ketimines: Construction of β-fluoroamine motifs with vicinal tetrasubstituted stereocenters

  2018cites this paper
• Copper-catalysed enantioselective Michael addition of malonic esters to β-trifluoromethyl-α,β-unsaturated imines.

  2017cites this paper
• Asymmetric synthesis of CF3-containing tetrahydroquinoline via a thiourea-catalyzed cascade reaction.

  2017cites this paper
• α-Trifluoromethylated tertiary homoallylic amines: diastereoselective synthesis and conversion into β-aminoesters, γ- and δ-aminoalcohols, azetidines and pyrrolidines.

  2017cites this paper
• Asymmetric Synthesis of α-Trifluoromethyl Pyrrolidines through Organocatalyzed 1,3-Dipolar Cycloaddition Reaction.

  2017cites this paper
• Direct Access to N-Unprotected α- and/or β-Tetrasubstituted Amino Acid Esters via Direct Catalytic Mannich-Type Reactions Using N-Unprotected Trifluoromethyl Ketimines.

  2017cites this paper
• Diarylprolinol as a Ligand for Enantioselective Alkynylation of Cyclic Imines

  2017cites this paper
• Organocatalytic Enantioselective Synthesis of Dihydropyrano‐ indole Derivatives Bearing Trifluoromethylated All‐Carbon‐ Substituted Stereocenters

  2017cites this paper
• Use of a (β‐Amidoallyl)boronate as a Nucleophilic Reagent in Catalytic Enantioselective Addition to Isatins

  2017cites this paper
• Chiral phosphoric acid catalyzed aza-Friedel-Crafts alkylation of indoles with cyclic aryl α-ketimino esters

  2017cites this paper
• Enantioselective alkynylation of N-sulfonyl α-ketiminoesters via a Friedel-Crafts alkylation strategy.

  2017cites this paper
• Direct access to N-unprotected tetrasubstituted propargylamines via direct catalytic alkynylation of N-unprotected trifluoromethyl ketimines.

  2017cites this paper
• α-Imino Esters in Organic Synthesis: Recent Advances.

  2017cites this paper
• Synthesis and Reactivity of Propargylamines in Organic Chemistry.

  2017cites this paper
• Synthesis of α-Ethynyl Glycines

  2016cites this paper
• Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides.

  2016cites this paper
• Development of a syn-Selective Mannich Reaction of Aldehydes with Propargylic Imines by Dual Catalysis: Asymmetric Synthesis of Functionalized Propargylic Amines.

  2016cites this paper
• The Synthesis of α,α-Disubstituted α-Amino Acids via Ichikawa Rearrangement.

  2016cites this paper
• Mechanistic Studies and Expansion of the Substrate Scope of Direct Enantioselective Alkynylation of α-Ketiminoesters Catalyzed by Adaptable (Phebox)Rhodium(III) Complexes.

  2016cites this paper
• Trifluoromethyl nitrogen heterocycles: synthetic aspects and potential biological targets.

  2016cites this paper
• Enantioselective, Copper-Catalyzed Alkynylation of Ketimines To Deliver Isoquinolines with α-Diaryl Tetrasubstituted Stereocenters.

  2016cites this paper
• Synthesis of Chiral Fluorinated Propargylamines via Chemoselective Biomimetic Hydrogenation.

  2016cites this paper
• Catalytic Enantioselective Conjugate Alkynylation of β-Aryl-β-trifluoromethyl Enones Constructing Propargylic All-Carbon Quaternary Stereogenic Centers.

  2016cites this paper
• Recent developments in asymmetric alkynylations

  2016cites this paper
• N-Boc-aminals as easily accessible precursors for less accessible N-Boc-imines: facile synthesis of optically active propargylamine derivatives using Mannich-type reactions

  2016cites this paper
• Biocatalytic Asymmetric Synthesis of Optically Pure Aromatic Propargylic Amines Employing ω-Transaminases

  2015cites this paper
• Recent Advances in Asymmetric Catalytic Methods for the Formation of Acyclic α,α-Disubstituted α-Amino Acids.

  2015cites this paper
• (R)‐1,1′‐Bi‐2,2′‐naphthol

  2015cites this paper
• Catalytic asymmetric synthesis of enantioenriched heterocycles bearing a C-CF3 stereogenic center.

  2015cites this paper
• Chiral Zinc Catalysts for Asymmetric Synthesis

  2015cites this paper
• Synthesis of Trifluoromethylated Analogues of 4,5‐Dihydroorotic Acid

  2015cites this paper
• Aldehyde–alkyne–amine (A3) coupling catalyzed by a highly efficient dicopper complex

  2015cites this paper
• Enantioselective Construction of Cyclic Indolyl α‐Amino Esters via a Friedel–Crafts Alkylation Reaction

  2015cites this paper
• Highly Stereoselective Synthesis of Terminal Chloro-Substituted Propargylamines and Further Functionalization.

  2015cites this paper
• Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines.

  2015cites this paper
• Trisubstituted 2-Trifluoromethyl Pyrrolidines via Catalytic Asymmetric Michael Addition/Reductive Cyclization

  2014cites this paper
• A recoverable Pd nanocatalyst for selective semi-hydrogenation of alkynes: hydrogenation of benzyl-propargylamines as a challenging model

  2014cites this paper
• Asymmetric alkynylation of seven-membered cyclic imines by combining chiral phosphoric acids and Ag(I) catalysts: synthesis of 11-substituted-10,11-dihydrodibenzo[b,f][1,4]oxazepine derivatives.

  2014cites this paper
• Asymmetric Synthesis of Quaternary α‐Amino Acids and Their Phosphonate Analogues

  2014cites this paper
• Catalytic Asymmetric 1,2-Alkynylation

  2013cites this paper