Enantioselective construction of quaternary stereogenic centers from tertiary boronic esters: methodology and applications.

No abstract is available for this paper.

• Publication year

  2011

• Venue

  Angewandte Chemie

• Publication date

  2011-04-11

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/anie.201008067PMID 21374774
• 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.

• Enantioselective synthesis of allylboronates bearing a tertiary or quaternary B-substituted stereogenic carbon by NHC-Cu-catalyzed substitution reactions.

  2010cited by this paper
• Homologation and alkylation of boronic esters and boranes by 1,2-metallate rearrangement of boronate complexes.

  2010cited by this paper
• Enantioselective synthesis of boron-substituted quaternary carbons by NHC-Cu-catalyzed boronate conjugate additions to unsaturated carboxylic esters, ketones, or thioesters.

  2010cited by this paper
• Metal-catalyzed asymmetric conjugate addition reaction: formation of quaternary stereocenters.

  2010cited by this paper
• Quaternary carbon stereogenic centers through copper-catalyzed enantioselective allylic substitutions with readily accessible aryl- or heteroaryllithium reagents and aluminum chlorides.

  2010cited by this paper
• Full chirality transfer in the conversion of secondary alcohols into tertiary boronic esters and alcohols using lithiation-borylation reactions.

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

  2010cited by this paper
• Enantioselective Route to Aryl(1,3‐butadien‐2‐yl)methanols: Formal Synthesis of (‐)‐Sporochnol A.

  2009cited by this paper
• Organocatalytic formation of quaternary stereocenters

  2009cited by this paper
• Synthesis of All-Carbon Quaternary Stereocenters

  2009cited by this paper
• Improved method for the conversion of pinacolboronic esters into trifluoroborate salts: facile synthesis of chiral secondary and tertiary trifluoroborates

  2009cited by this paper
• Enantiodivergent conversion of chiral secondary alcohols into tertiary alcohols

  2008cited by this paper
• Asymmetric catalysis for the construction of quaternary carbon centres: nucleophilic addition on ketones and ketimines.

  2007cited by this paper
• Enantioselective synthesis of a trans-7,8-dimethoxycalamenene.

  2007cited by this paper
• Enantioselective Catalytic Formation of Quaternary Stereogenic Centers

  2007cited by this paper
• Creation of quaternary stereocenters in carbonyl allylation reactions.

  2007cited by this paper
• A short and efficient synthesis of (R)-(−)-sporochnol A

  2006cited by this paper
• Chiral phosphoramide-catalyzed enantioselective addition of allylic trichlorosilanes to aldehydes. Preparative studies with bidentate phosphorus-based amides.

  2006cited by this paper
• Catalytic Enantioselective Construction of All‐Carbon Quaternary Stereocenters

  2006cited by this paper
• Stereoselective Construction of Quaternary Stereocenters

  2005cited by this paper
• Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

  2004cited by this paper
• Construction of quaternary stereocenters: new perspectives through enantioselective Michael reactions.

  2003cited by this paper
• Migratory aptitudes of simple alkyl groups in the anionotropic rearrangement of quaternary chloromethyl borate species: a combined experimental and theoretical investigation.

  2003cited by this paper
• Aufbau quartärer Stereozentren: neue Möglichkeiten durch enantioselektive Michael‐Reaktion

  2003cited by this paper
• Asymmetric construction of quaternary centers by enantioselective allylation: application to the synthesis of the serotonin antagonist LY426965.

  2002cited by this paper
• Total synthesis of sporochnols, fish deterrents from a marine alga

  2002cited by this paper
• Enantioselektiver Aufbau quartärer Stereozentren

  2001cited by this paper
• Enantioselective Construction of Quaternary Stereocenters.

  2001cited by this paper
• Remarkable effect of aluminum reagents on rearrangements of epoxy acylates via stable cation intermediates and its application to the synthesis of (S)-(+)-sporochnol A.

  2001cited by this paper
• Modular Pyridinyl Peptide Ligands in Asymmetric Catalysis: Enantioselective Synthesis of Quaternary Carbon Atoms Through Copper-Catalyzed Allylic Substitutions.

  2001cited by this paper
• The novel 5-Hydroxytryptamine(1A) antagonist LY426965: effects on nicotine withdrawal and interactions with fluoxetine.

  2000cited by this paper
• Total synthesis of (−)-sporochnol A, the fish deterrent, from a chiral malonate

  1999cited by this paper
• α-Halo boronic esters in asymmetric synthesis

  1998cited by this paper
• The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters.

  1998cited by this paper
• Der katalytische enantioselektive Aufbau von Molekülen mit quartären Kohlenstoff‐Stereozentren

  1998cited by this paper
• The absolute configuration of (+)-sporochnol A, the fish deterrent from the Caribbean marine alga Sporochnus bolleanus

  1997cited by this paper
• Homologation of representative boronic esters using in situ generated (halomethyl)lithiums: A comparative study

  1994cited by this paper
• Asymmetric creation of quaternary carbon centers

  1993cited by this paper
• Organoboranes. 57. Relative efficacy of representative lithium dialkylamide bases for the in situ metalation of allyl chloride to produce (.alpha.-chloroallyl)lithium. Application of the reagent to B-alkoxy-9-borabicyclononanes producing new routes to interesting cyclooctane derivatives

  1993cited by this paper
• Secondary metabolite chemistry of the caribbean marine alga Sporochnus bolleanus: A basis for herbivore chemical defence

  1992cited by this paper
• Organoboranes. 54. Exploration of the reactions of (.alpha.-haloallyl)lithium with organoborane derivatives. Simple and convenient procedure for the synthesis of three-carbon homologated boronate esters and terminal alkenes

  1992cited by this paper
• Preparation and 1-carbon homologation of boronic ester substituted Δ2-isoxazolines: The 1,3 dipolar cycloaddition of nitrile oxides to vinyl boronic esters

  1992cited by this paper
• Asymmetric synthesis of tertiary alcohols from α-halo boronic esters

  1990cited by this paper
• Asymmetric Synthesis of the Four Stereoisomers of 4-Methyl-3-heptanol via Boronic Esters: Sequential Double Stereodifferentiation Leads to Very High Purity

  1990cited by this paper
• (Chloromethyl)lithium: efficient generation and capture by boronic esters and a simple preparation of diisopropyl (chloromethyl)boronate

  1985cited by this paper
• Homologation of boronic esters to α-chloro boronic esters

  1983cited by this paper
• Relative migratory aptitudes of alkyl groups in the iodination of ethenyltrialkylborates. A conformational analysis

  1982cited by this paper
• .alpha.-Chloro boronic esters from homologation of boronic esters

  1980cited by this paper
• Studies directed toward the synthesis of prostaglandins. Useful boron-mediated olefin syntheses.

  1976cited by this paper
• A stereoselective synthesis of conjugated dienes from alkynes via the hydroboration-iodination reaction

  1968cited by this paper
• A convenient stereoselective synthesis of substituted alkenes via hydroboration-iodination of alkynes

  1967cited by this paper

• Construction of Chiral β-Boryl Aldehydes via Asymmetric Hydroformylation of 1,1-Disubstituted Alkenyl Boronates.

  2026cites this paper
• Synthesis of Acyclic α-Quaternary Chiral Nitriles via Ni-Catalyzed Asymmetric Markovnikov Hydrocyanation of 1,1-Disubstituted and Trisubstituted Alkenes.

  2026cites this paper
• Recent Advances in Stereospecific Transformations of Organoboron Reagents

  2025cites this paper
• Iridium-Catalyzed Asymmetric Allylic Alkylation of Boron Enolates to Construct Acyclic All-Carbon Quaternary Stereocenters.

  2025cites this paper
• Syntheses of Marine Natural Products via Matteson Homologations and Related Processes

  2025influential citation
• Recent advances in the construction of quaternary pseudoanomeric centers in gem-C,C-glycosides: from zaragozic acids to remdesivir.

  2025cites this paper
• Catalytic asymmetric isomerization/hydroboration of silyl enol ethers

  2025cites this paper
• Copper-catalyzed stereospecific methoxyboration of styrenes enabled by oxygen umpolung with acetal-based peroxides

  2025cites this paper
• 1,2-Migratory ring expansion of a BN-naphthalene

  2025cites this paper
• Enantiodivergent Rh-Catalyzed Reductive Hydroformylation of Alkenyl Boronic Esters.

  2025cites this paper
• Electronic Activation Enables the Borylation of Alkyl C-H Bonds in Saturated Nitrogen Heterocycles.

  2025cites this paper
• Rhodium-Catalyzed Asymmetric Remote C(sp3)-H Borylation of Aldehyde-Derived Silyl Enol Ethers.

  2025cites this paper
• [1,3]-Hydride Shift in α-Boryl Cations: Strategic Design of Fluorine-Triggered Cyclopropanation.

  2025cites this paper
• Diastereoselective Synthesis of Cyclopropyl Diboronates via 1,2-Boronate Rearrangement.

  2025cites this paper
• Cu/Ir Relay Catalysis for Regio- and Enantioselective Alkene Borylation/Allylic Alkylation.

  2025cites this paper
• Migratory olefination of tertiary boronic esters under Matteson homologation conditions

  2025cites this paper
• Zn-Mediated Fragmentation of β-Boryl NHPI Esters Enabling the Radical 1,2-Boron Shift for the Synthesis of gem-Difluoroalkenyl Boronates.

  2025cites this paper
• Synthesis of Chiral δ-Aminoboronic Esters by Enantioselective Hydrogenation of 1,2-Azaborines.

  2025cites this paper
• Asymmetric Construction of a SeCF3-Substituted Stereocenter by CuH-Catalyzed Hydroboration of 1-SeCF3-Alkenes.

  2025cites this paper
• Photoinduced Assembly of Diverse Homoallylic Boronates from gem-Diborons.

  2025cites this paper
• Asymmetric Radical Cyclopropanation of α,β-Unsaturated Amides with α-Boryl and α-Silyl Dibromomethanes via Cr(II)-Based Metalloradical Catalysis.

  2025cites this paper
• Asymmetric dihydroboration of allenes enabled by ligand relay catalysis

  2024cites this paper
• Cooperative Cu/Pd-Catalyzed 1,5-Boroacylation of Cyclopropyl-Substituted Alkylidenecyclopropanes.

  2024cites this paper
• Triply Selective & Sequential Diversification at Csp3: Expansion of Alkyl Germane Reactivity for C-C & C-Heteroatom Bond Formation.

  2024cites this paper
• Enantioselective synthesis of multifunctional alkylboronates via N-heterocyclic carbene–nickel-catalysed carboboration of alkenes

  2024cites this paper
• Asymmetric Synthesis of SCF3-Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes.

  2024cites this paper
• Iridium-Catalyzed Enantioselective Vinylogous and Bisvinylogous Allenylic Substitution

  2024cites this paper
• Boron Ylide Enables Stereoselective Construction of gem-Diborylcyclopropanes.

  2024cites this paper
• Catalytic Contra-Thermodynamic Isomerization–Asymmetric Hydroboration of Alkenyl Alcohols and Amines

  2024cites this paper
• A General Method to Access Sterically Encumbered Geminal Bis(boronates) via Formal Umpolung Transformation of Terminal Diboron Compounds.

  2023cites this paper
• Kinetic Resolution of Aldehydes Bearing an All-Carbon Quaternary Stereocenter at the α-Position by the Antilla Allylboration

  2023cites this paper
• Desymmetrization of Cyclohexadienones Containing a Quaternary γ-Carbon Atom by Conjugate Addition of Boron Nucleophiles

  2023cites this paper
• Copper-Catalyzed Diastereoselective Borylative Allylation of Alkenyl Sulfones and Base-Controlled Synthesis of Skipped Dienes.

  2023cites this paper
• Synthesis of substituted benzylboronates by light promoted homologation of boronic acids with N-sulfonylhydrazones

  2023cites this paper
• Stereoselective Construction of β-chiral Homoallyl Functionalities by Substrate- and Reagent-Controlled Iterative 1,2-Metallate Rearrangements

  2023cites this paper
• Reaction of 4-Bpin-o-Carborane with Ketones: Sequential Carbon Vertex Alkylation and B-B Bond Activation.

  2023cites this paper
• Enantioselective Construction of Carbocyclic and Heterocyclic Tertiary Boronic Esters by Conjunctive Cross-Coupling Reaction.

  2023cites this paper
• Transition metal-free visible light photoredox-catalyzed remote C(sp3)−H borylation enabled by 1,5-hydrogen atom transfer

  2023cites this paper
• Anion-Mediated, Stereospecific Synthesis of Secondary and Tertiary Cyclopropylboronates from Chiral Epoxides and gem-Diborylalkanes.

  2023cites this paper
• Synthesis of α-Haloboronates by the Halogenation of gem-Diborylalkanes via Tetracoordinate Boron Species.

  2023cites this paper
• Facile Access to Cyclopropylboronates via Stereospecific Deborylative Cyclization: A Leaving Group-Assisted Activation of Geminal Diborons.

  2023cites this paper
• Photosensitized [2+2]-Cycloadditions of Alkenylboronates and Alkenes.

  2022cites this paper
• Ni-Catalyzed Radical-Promoted Defluoroalkylborylation of Trifluoromethyl Alkenes To Access gem-Difluorohomoallylic Boronates.

  2022cites this paper
• Enantioselective synthesis of cyclic α-aminoboronates via copper-catalyzed dearomative borylation of 4-quinolinols.

  2022cites this paper
• Transition Metal Catalyst Free Synthesis of Olefins from Organoboron Derivatives

  2022cites this paper
• Stereoselective gem-C,B-Glycosylation via 1,2-Boronate Migration.

  2022cites this paper
• Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes

  2022cites this paper
• Enantio- and diastereoselective boron conjugate addition to α-alkyl α,β-unsaturated esters.

  2022cites this paper
• anti-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters

  2022cites this paper
• Ligand-Enabled Copper-Catalyzed Regio- and Stereoselective Allylboration of 1-Trifluoromethylalkenes.

  2022cites this paper
• Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters.

  2022cites this paper
• Cobalt-Catalyzed Remote Hydroboration of Alkenyl Amines.

  2021cites this paper
• Stereodivergent Nucleophilic Additions to Racemic β-Oxo Acid Derivatives: Fast Addition Outcompetes Stereoconvergence in the Archetypal Configurationally Unstable Electrophile.

  2021cites this paper
• Nickel/Enamine Cooperative Catalysis Enables Highly Enantioselective Allylic Alkylation of α-Branched Aldehydes

  2021cites this paper
• sp3 Bis-Organometallic Reagents via Catalytic 1,1-Difunctionalization of Unactivated Olefins.

  2021cites this paper
• Copper(I)-Catalyzed Asymmetric Conjugate 1,6-, 1,8-, and 1,10-Borylation.

  2021cites this paper
• Enantioselective catalytic 1,2-boronate rearrangements

  2021cites this paper
• Dual Ni/photoredox-catalyzed asymmetric cross-coupling to access chiral benzylic boronic esters

  2021cites this paper
• Access to enantioenriched compounds bearing challenging tetrasubstituted stereocenters via kinetic resolution of auxiliary adjacent alcohols

  2021cites this paper
• The Matteson Reaction

  2021cites this paper
• Rhodium-Catalyzed Regiodivergent Synthesis of Alkylboronates via Deoxygenative Hydroboration of Aryl Ketones: Mechanism and Origin of Selectivities

  2021cites this paper
• Iridium-Catalyzed Regio- and Enantioselective Borylation of Unbiased Methylene C(sp3)-H Bonds at the Position Beta to a Nitrogen Center.

  2020cites this paper
• Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications†

  2020cites this paper
• Stereoselective [4+2]-Cycloaddition with Chiral Alkenylboranes.

  2020cites this paper
• Stereodivergent Asymmetric Synthesis of α,β-Disubstituted β Aminoalkylboronic Acid Derivatives via Group-Selective Protodeboronation Enabling Access to the Elusive anti Isomer.

  2020cites this paper
• Iridium-Catalyzed γ-Selective Hydroboration of γ-Substituted Allylic Amides.

  2020cites this paper
• Desymmetrization of C 2‐Symmetric Bis(Boronic Esters) by Zweifel Olefinations

  2020cites this paper
• Site-Selective 1,2-Dicarbofunctionalization of Vinyl Boronates via Dual Catalysis.

  2020cites this paper
• FMPhos: Expanding the Catalytic Capacity of Small-Bite-Angle Bisphosphine Ligands in Regioselective Alkene Hydrofunctionalizations

  2020cites this paper
• β-Silyloxy Allylboronate Esters through an Aldehyde Borylation/Homologation Sequence.

  2020cites this paper
• Multifaceted Substrate-Ligand Interactions Promote the Copper-Catalyzed Hydroboration of Benzylidenecyclobutanes and Related Compounds.

  2020cites this paper
• Drosophila fabp is required for light-dependent Rhodopsin-1 clearance and photoreceptor survival

  2020cites this paper
• Asymmetric Conjugate Addition of Chiral Secondary Borylalkyl Copper Species.

  2020cites this paper
• Site‐Selective 1,2‐Dicarbofunctionalization of Vinyl Boronates through Dual Catalysis

  2020cites this paper
• Iridium-Catalyzed Enantioselective Unbiased Methylene C(sp3)-H Borylation of Acyclic Amides.

  2020cites this paper
• Electrophilic fluoroalkylthiolation induced diastereoselective and stereospecific 1,2-metalate migration of alkenylboronate complexes†

  2020cites this paper
• Synthesis and Applications of β‐Aminoalkylboronic Acid Derivatives

  2020cites this paper
• Transition metal-free synthesis of alkyl pinacol boronates.

  2020cites this paper
• Stereospecific 1,2‐Migrations of Boronate Complexes Induced by Electrophiles

  2020cites this paper
• Ligand-Controlled Regiodivergent Enantioselective Rhodium-Catalyzed Alkene Hydroboration.

  2019cites this paper
• Access to Benzylic Quaternary Carbons from Aromatic Ketones.

  2019cites this paper
• Catalytic Asymmetric Conjugate Addition of Borylalkyl Copper Complex in Chiral Organoboronate Synthesis.

  2019cites this paper
• Remote, Diastereoselective Cobalt-Catalyzed Alkene Isomerization–Hydroboration: Access to Stereodefined 1,3-Difunctionalized Indanes

  2019cites this paper
• High-Throughput Ligand Screening Enables the Enantioselective Conjugate Borylation of Cyclobutenones to Access Synthetically Versatile Tertiary Cyclobutylboronates.

  2019cites this paper
• Rhodium-Catalyzed Remote C(sp3)-H Borylation of Silyl Enol Ethers Jie Li, Shuanglin Qu, and Wanxiang Zhao.

  2019cites this paper
• Facile access to functionalized chiral secondary benzylic boronic esters via catalytic asymmetric hydroboration

  2019cites this paper
• Radical Addition to Strained σ-Bonds Enables the Stereocontrolled Synthesis of Cyclobutyl Boronic Esters.

  2019cites this paper
• Ring-Opening Lithiation-Borylation of 2-Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters.

  2019cites this paper
• Strain Release of Donor-Acceptor Cyclopropyl Boronate Complexes.

  2019cites this paper
• Iridium-Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes.

  2019cites this paper
• Base-catalysed reductive relay hydroboration of allylic alcohols with pinacolborane to form alkylboronic esters.

  2019cites this paper
• Synthesis of α‐Quaternary Aldehydes via a Stereoselective Semi‐Pinacol Rearrangement of Optically Active Epoxy Alcohols

  2019cites this paper
• Synthesis of (±)-Idarubicinone via Global Functionalization of Tetracene.

  2019cites this paper
• Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Cyclopropanes.

  2019cites this paper
• Pd(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol via a Chiral Auxiliary.

  2019cites this paper
• Copper-Catalyzed Asymmetric Defluoroborylation of 1-(Trifluoromethyl)Alkenes

  2018cites this paper
• Stereocontrolled Synthesis of Polypropionate Fragments based on a Building Block Assembly Strategy using Lithiation-Borylation Methodologies.

  2018cites this paper
• Copper-Catalyzed Diastereo- and Enantioselective Borylative Cyclization: Synthesis of Enantioenriched 2,3-Disubstituted Indolines.

  2018cites this paper
• A Modular Approach to the Synthesis of gem-Disubstituted Cyclopropanes.

  2018cites this paper
• Copper-Catalyzed Enantioselective Markovnikov Protoboration of α-Olefins Enabled by a Buttressed N-Heterocyclic Carbene Ligand.

  2018cites this paper