Enantioselective bromination/semipinacol rearrangement for the synthesis of β-bromoketones containing an all-α-carbon quaternary center

No abstract is available for this paper.

• Publication year

  2011

• Venue

  Chemical Science

• Publication date

  2011-08-08

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1039/C1SC00295C
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• Organocatalytic asymmetric halogenation/semipinacol rearrangement: highly efficient synthesis of chiral α-oxa-quaternary β-haloketones.

  2011cited by this paper
• On the chlorenium source in the asymmetric chlorolactonization reaction.

  2011cited by this paper
• Aminothiocarbamate-catalyzed asymmetric bromolactonization of 1,2-disubstituted olefinic acids.

  2011cited by this paper
• Ring expansion of cyclobutylmethylcarbenium ions to cyclopentane or cyclopentene derivatives and metal-promoted analogous rearrangements.

  2011cited by this paper
• Direct asymmetric bromination of aldehydes catalyzed by a binaphthyl-based secondary amine: highly enantio- and diastereoselective one-pot synthesis of bromohydrins.

  2010cited by this paper
• Enantioselective halocyclization reactions for the synthesis of chiral cyclic compounds.

  2010cited by this paper
• Catalytic asymmetric bromoamination of chalcones: highly efficient synthesis of chiral alpha-bromo-beta-amino ketone derivatives.

  2010cited by this paper
• Enantioselective bromolactonization of conjugated (Z)-enynes.

  2010cited by this paper
• Asymmetric bromolactonization using amino-thiocarbamate catalyst.

  2010cited by this paper
• Chiral Brønsted acid catalyzed pinacol rearrangement.

  2010cited by this paper
• Asymmetric bromolactonization catalyzed by a C3-symmetric chiral trisimidazoline.

  2010cited by this paper
• An organocatalytic asymmetric chlorolactonization.

  2010cited by this paper
• Organocatalytic formation of quaternary stereocenters

  2009cited by this paper
• Trends in organocatalytic conjugate addition to enones: an efficient approach to optically active alkynyl, alkenyl, and ketone products.

  2009cited by this paper
• Gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols.

  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
• Organocascade reactions of enones catalyzed by a chiral primary amine.

  2009cited by this paper
• Design and Application of 2,2‐Dibromodimedone as Organic Brominating Reagent for Asymmetric Bromination of 1,3‐Dicarbonyl Compounds and Ketones Catalysed by Chiral Amino Acids

  2009cited by this paper
• Brønsted Acid catalyzed enantioselective semipinacol rearrangement for the synthesis of chiral spiroethers.

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

  2009cited by this paper
• Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts.

  2008cited by this paper
• Palladium-catalyzed diastereo- and enantioselective Wagner-Meerwein shift: control of absolute stereochemistry in the C-C bond migration event.

  2008cited by this paper
• Synthetic studies toward halichlorine: complex azaspirocycle formation with use of an NBS-promoted semipinacol reaction.

  2008cited by this paper
• Total synthesis of complex cyclotryptamine alkaloids: stereocontrolled construction of quaternary carbon stereocenters.

  2007cited by this paper
• Recent advances in the semi-pinacol rearrangement of α-hydroxy epoxides and related compounds

  2007cited by this paper
• Catalytic Enantioselective Construction of All‐Carbon Quaternary Stereocenters

  2006cited by this paper
• Total synthesis of (+/-)-galanthamine.

  2006cited by this paper
• Palladium-catalyzed asymmetric ring expansion of allenylcyclobutanols: an asymmetric Wagner-Meerwein shift.

  2006cited by this paper
• Scalable Methodology for the Catalytic, Asymmetric α-Bromination of Acid Chlorides

  2006cited by this paper
• Organocatalytic asymmetric α-bromination of aldehydes and ketones

  2005cited by this paper
• Organocatalytic Asymmetric α-Halogenation of 1,3-Dicarbonyl Compounds

  2005cited by this paper
• Stereoselective Construction of Quaternary Stereocenters

  2005cited by this paper
• Quinine/selectfluor combination induced asymmetric semipinacol rearrangement of allylic alcohols: an effective and enantioselective approach to alpha-quaternary beta-fluoro aldehydes.

  2005cited by this paper
• Asymmetric organic catalysis with modified cinchona alkaloids.

  2004cited by this paper
• A tandem semipinacol rearrangement/alkylation of alpha-epoxy alcohols: an efficient and stereoselective approach to multifunctional 1,3-diols.

  2004cited by this paper
• An efficient total synthesis of (+/-)-lycoramine.

  2004cited by this paper
• Synthesis of functionalized 1-azaspirocyclic cyclopentanones using bronsted acid or N-bromosuccinimide promoted ring expansions.

  2004cited by this paper
• Catalytic Asymmetric Bromination and Chlorination of β‐Ketoesters

  2004cited by this paper
• Stereoselective Formation of Quaternary Carbon Centers and Related Functions

  2003cited by this paper
• Lewis acid promoted highly stereoselective rearrangement of 2,3-aziridino alcohols: a new efficient approach to beta-amino carbonyl compounds.

  2002cited by this paper
• Samarium-Catalyzed Tandem Semipinacol Rearrangement/Tishchenko Reaction of α-Hydroxy Epoxides: A Novel Approach to Highly Stereoselective Construction of 2-Quaternary 1,3-Diol Units.

  2001cited by this paper
• Reactive ketenes through a carbonate/amine shuttle deprotonation strategy: catalytic, enantioselective alpha-bromination of acid chlorides.

  2001cited by this paper
• A highly enantioselective chiral Lewis base-catalyzed asymmetric cyanation of ketones.

  2001cited by this paper
• 1-Oxaspiro[4.4]nonan-6-ones. Synthetic access via oxonium ion technology, optical resolution, and conversion into enantiopure spirocyclic alpha,beta-butenolides.

  2001cited by this paper
• A catalytic asymmetric Wagner-Meerwein shift.

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

  2001cited by this paper
• A Highly Enantioselective Catalytic Desymmetrization of Cyclic Anhydrides with Modified Cinchona Alkaloids

  2000cited by this paper
• Stereoselective Reductive Rearrangement of α-Hydroxy Epoxides: A New Method for Synthesis of 1,3-Diols1

  1999cited by this paper
• The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters.

  1998cited by this paper
• Asymmetric creation of quaternary carbon centers

  1993cited by this paper

• Straightforward construction of functionalized γ-lactams via conjugated-engineered covalent organic framework photocatalysed cascade reactions

  2025cites this paper
• Room-Temperature Secondary Ammonium Salt-Catalyzed Enantioselective Halogenation via Hydrogen-Bonded Ion Pair

  2024cites this paper
• Asymmetric Bromination/Semipinacol Rearrangement Enabled by Brønsted Acids of Stereogenic-at-Cobalt(III) Complexes.

  2024cites this paper
• Cross-assembly confined bifunctional catalysis via non-covalent interactions for asymmetric halogenation

  2023cites this paper
• Advances in Radical Mediated 1,2-Aryl Migration Reactions of α,α-Diarylallyl Alcohols

  2023cites this paper
• Two Green Protocols for Halogenative Semipinacol Rearrangement.

  2022cites this paper
• Enantioselective halogenation via asymmetric phase‐transfer catalysis

  2022cites this paper
• Catalytic Enantioselective 5-Endo-Bromocycloetherification of Unactivated Cyclic Alkenes

  2022cites this paper
• Asymmetric Semipinacol Rearrangement Enabled by Copper-Catalyzed Propargylic Alkylation

  2022cites this paper
• On the Importance of Halogen Bonding Interactions in Two X-ray Structures Containing All Four (F, Cl, Br, I) Halogen Atoms

  2021cites this paper
• Enantioselective Halofunctionalization of Alkenes

  2021cites this paper
• Organoiodine-induced hydroxylation as well as enantioselective alkoxylation/hydroxylation of allylic alcohols via 1,2- aryl migration

  2021cites this paper
• Cu2O-catalyzed phosphonyldifluoromethylation of allylic alcohols through a radical 1,2-aryl migration

  2020cites this paper
• Catalytic Enantioselective Bromoaminocyclization and Bromocycloetherification

  2020cites this paper
• Ritter-enabled catalytic asymmetric chloroamidation of olefins

  2020cites this paper
• Fluoroalkylation of Allylic Alcohols with Concomitant (Hetero)aryl Migration: Access to Fluoroalkylated Ketones and Evaluation of Antifungal Action against Magnaporthe grisea

  2020cites this paper
• Divergent Synthesis of Trifluoromethyl Sulfoxides and β-SCF3 Carbonyl Compounds by Tandem Trifluoromethylthiolation/Rearrangement of Allylic and Propargylic Alcohols.

  2020cites this paper
• Enantioselective Catalytic Aldehyde α-Alkylation/Semipinacol Rearrangement: Construction of α-Quaternary-δ-Carbonyl Cycloketones and Total Synthesis of (+)-Cerapicol.

  2020cites this paper
• Enantioselective Syntheses of α‐ exo ‐Methylene‐Lactones via Organocatalytic Halolactonization

  2019cites this paper
• A copper-catalyzed radical coupling/fragmentation reaction: efficient access to β-oxophosphine oxides

  2019cites this paper
• Electrochemical halogenation/semi-pinacol rearrangement of allylic alcohols using inorganic halide salt: an eco-friendly route to the synthesis of β-halocarbonyls

  2019cites this paper
• Enantioselective Halolactonizations Using Amino-Acid-Derived Phthalazine Catalysts.

  2019cites this paper
• Facial Syntheses of Bromobenzothiazines via Catalyst-Free Tandem C-H Amination/Bromination in Water.

  2019cites this paper
• Halogen bonding in Wagner-Meerwein rearrangement products

  2018cites this paper
• Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones

  2018cites this paper
• Recent Advances in the Synthesis of β-Functionalized Ketones by Radical-Mediated 1,2-Rearrangement of Allylic Alcohols.

  2018cites this paper
• Oxidative acylation of α,α-diarylallylic alcohols: Synthesis of 1,2,4-triarylbutane-1,4-diones

  2018cites this paper
• Catalyst-free tandem halogenation/semipinacol rearrangement of allyl alcohols with sodium halide in water

  2018cites this paper
• Catalytic enantioselective bromohydroxylation of aryl olefins with flexible functionalities

  2017cites this paper
• Enantioselective Chloro‐O‐cyclization of Unsaturated N‐Tosylcarbamates

  2017cites this paper
• α-Quaternary Mannich Bases through Copper-Catalyzed Amination-Induced 1,2-Rearrangement of Allylic Alcohols.

  2017cites this paper
• Accessing Axially Chiral Biaryls via Organocatalytic Enantioselective Dynamic-Kinetic Resolution-Semipinacol Rearrangement

  2017cites this paper
• 7. Synthesis of Organohalides

  2016cites this paper
• Monomeric Cinchona Alkaloid-Based Catalysts for Highly Enantioselective Bromolactonisation of Alkynes.

  2016cites this paper
• Highly Enantioselective Bromocyclization of Allylic Amides with a P/P=O Double-Site Lewis Base Catalyst.

  2016cites this paper
• Phosphine Oxide-Sc(OTf)3 Catalyzed Highly Regio- and Enantioselective Bromoaminocyclization of (E)-Cinnamyl Tosylcarbamates. An Approach to a Class of Synthetically Versatile Functionalized Molecules.

  2016cites this paper
• Recent advances in terpenoid syntheses from China

  2016cites this paper
• Catalytic Asymmetric Bromination of Unfunctionalized Olefins with H2O as a Nucleophile.

  2015cites this paper
• Radical 1,2-aryl migration in α,α-diaryl allylic alcohols toward β-silyl ketones.

  2015cites this paper
• Enantioselective 6-exo-Bromoaminocyclization of Homoallylic N-Tosylcarbamates Catalyzed by a Novel Monophosphine-Sc(OTf)3 Complex.

  2015cites this paper
• Pinacol and Semipinacol Rearrangements in Total Synthesis

  2015cites this paper
• Chiral Phosphine Oxide-Sc(OTf)3 Complex Catalyzed Enantioselective Bromoaminocyclization of 2-Benzofuranylmethyl N-Tosylcarbamates. Approach to a Novel Class of Optically Active Spiro Compounds.

  2015cites this paper
• Visible light promoted carbodifluoroalkylation of allylic alcohols via concomitant 1,2-aryl migration.

  2015cites this paper
• Catalytic Asymmetric Construction of α-Quaternary Cyclopentanones and Its Application to the Syntheses of (-)-1,14-Herbertenediol and (-)-Aphanorphine.

  2015cites this paper
• Domino Michael-Michael and Aldol-Aldol Reactions: Diastereoselective Synthesis of Functionalized Cyclohexanone Derivatives Containing Quaternary Carbon Center.

  2015cites this paper
• Visible-light-mediated photocatalytic difluoroalkylation/1,2-carbon migration sequences: synthesis of difluoroalkyl-substituted cyclic ketones

  2015cites this paper
• Enantioselective bromocyclization of allylic amides catalyzed by BINAP derivatives.

  2015cites this paper
• Organocatalytic asymmetric chlorinative dearomatization of naphthols

  2015cites this paper
• Copper-catalyzed cyanomethylation of allylic alcohols with concomitant 1,2-aryl migration: efficient synthesis of functionalized ketones containing an α-quaternary center.

  2015cites this paper
• Enantioselective halogenative semi-pinacol rearrangement: extension of substrate scope and mechanistic investigations.

  2015cites this paper
• A nickel-mediated oxidative α-C(sp(3))-H functionalization of amides with allylic alcohols terminated by radical 1,2-aryl migration.

  2015cites this paper
• Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides.

  2015cites this paper
• Cinchona Alkaloids as Organocatalysts in Enantioselective Halofunctionalization of Alkenes and Alkynes

  2014cites this paper
• Asymmetric semipinacol rearrangement of 2,3-allenols with N-bromo-1,8-naphthalimide.

  2014cites this paper
• Asymmetric chlorination/ring expansion for the synthesis of α-quaternary cycloalkanones.

  2014cites this paper
• Catalytic asymmetric semipinacol rearrangements.

  2014cites this paper
• Asymmetric chlorocyclization of indole-3-yl-benzamides for the construction of fused indolines.

  2014cites this paper
• Enantioselective halogenative semi-pinacol rearrangement: a stereodivergent reaction on a racemic mixture.

  2014cites this paper
• Lewis base mediated halogenation/semipinacol rearrangement of diazo compounds: new access to α-halo-quaternary ketones.

  2014cites this paper
• Formal Asymmetric Hydrobromination of Styrenes via Copper-Catalyzed 1,3-Halogen Migration.

  2014cites this paper
• Silver-catalyzed carbonphosphonation of α,α-diaryl allylic alcohols: synthesis of β-aryl-γ-ketophosphonates.

  2014cites this paper
• 3.16 The Semipinacol Rearrangements

  2014cites this paper
• Chiral‐Amine‐Catalyzed Asymmetric Bromocyclization of Tryptamine Derivatives

  2014cites this paper
• 7.21 Addition Reactions with Formation of CarbonHalogen Bonds

  2014cites this paper
• Catalytic asymmetric intermolecular bromoesterification of unfunctionalized olefins.

  2014cites this paper
• Synthesis of β-Haloketones by β-Addition Reactions of α,β-Unsaturated Ketones with BX3 (X = Br, Cl) as Halide Source

  2014cites this paper
• Recent advances in asymmetric intra- and intermolecular halofunctionalizations of alkenes.

  2014cites this paper
• Brønsted Acid Catalyzed Phosphoramidic Acid Additions to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations for the Synthesis of C- and P-Chiral Phosphoramidates

  2014cites this paper
• Enantioselective, desymmetrizing bromolactonization of alkynes.

  2013cites this paper
• Rhodium/chiral urea relay catalysis enables an enantioselective semipinacol rearrangement/Michael addition cascade.

  2013cites this paper
• Cinchonas and cupreidines

  2013cites this paper
• Prediction of suitable catalyst by 1H NMR: asymmetric synthesis of multisubstituted biaryls by chiral phosphoric acid catalyzed asymmetric bromination

  2013cites this paper
• Enantioselective intermolecular bromoesterification of allylic sulfonamides

  2013cites this paper
• Carbon–Halogen Bond Formation

  2013cites this paper
• C2-symmetric cyclic selenium-catalyzed enantioselective bromoaminocyclization.

  2013cites this paper
• Enantioselective synthesis of multisubstituted biaryl skeleton by chiral phosphoric acid catalyzed desymmetrization/kinetic resolution sequence.

  2013cites this paper
• Enantioselective organocatalytic iodination-initiated Wagner-Meerwein rearrangement.

  2013cites this paper
• Kinetic resolution of unsaturated amides in a chlorocyclization reaction: concomitant enantiomer differentiation and face selective alkene chlorination by a single catalyst.

  2013cites this paper
• Enantioselective organocatalytic fluorination-induced Wagner-Meerwein rearrangement.

  2013cites this paper
• Catalytic, enantioselective, and highly chemoselective bromocyclization of olefinic dicarbonyl compounds.

  2013cites this paper
• Recent Progress in Organocatalytic Asymmetric Halocyclization

  2013cites this paper
• Formal synthesis of (-)-cephalotaxine based on a tandem hydroamination/semipinacol rearrangement reaction.

  2012cites this paper
• Organocatalytic asymmetric fluorination/semipinacol rearrangement: an efficient approach to chiral β-fluoroketones.

  2012cites this paper
• New catalytic approaches towards the enantioselective halogenation of alkenes.

  2012cites this paper
• Platinum-catalyzed cyclization/[1,2]-alkyl migration/allyl shift/cyclization cascade of epoxy alkynyl allyl ethers: a step-economical route to spirobenzo[h]chromanones.

  2012cites this paper
• Catalytic enantioselective halolactonization of enynes and alkenes.

  2012cites this paper
• An enantioselective approach toward 3,4-dihydroisocoumarin through the bromocyclization of styrene-type carboxylic acids.

  2012cites this paper
• Enantioselective bromolactonization using an S-alkyl thiocarbamate catalyst.

  2012cites this paper
• Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed iodolactonization.

  2012cites this paper
• Enantioselective halocyclization using reagents tailored for chiral anion phase-transfer catalysis.

  2012cites this paper
• Enantioselective bromocyclization of olefins catalyzed by chiral phosphoric acid.

  2011cites this paper
• Enantioselective Bromination/Semipinacol Rearrangement for the Synthesis of β‐Bromoketones Containing an All‐α‐carbon Quaternary Center.

  2011cites this paper