Combining Organocatalysis with Central‐to‐Axial Chirality Conversion: Atroposelective Hantzsch‐Type Synthesis of 4‐Arylpyridines
Angewandte Chemie International EditionPublished 14 December 2015
Ophélie Quinonero, Marion Jean, Nicolas Vanthuyne, Christian Roussel, Damien Bonne, Thierry Constantieux
Citations170
SJR quartileQ1
SJR score5.55
SNIP2.47
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
TL;DR
Suitably substituted enantioenriched 4-aryl-1,4-dihydro-pyridines prepared by an organocatalytic enantioselective Michael addition were oxidized with MnO2 into axially chiral 4-arylpyridine with central-to-axial chirality conversion.
Abstract
Suitably substituted enantioenriched 4-aryl-1,4-dihydro-pyridines prepared by an organocatalytic enantioselective Michael addition were oxidized with MnO2 into axially chiral 4-arylpyridines with central-to-axial chirality conversion. Moderate to complete percentages (cp) were observed, and a model for the conversion of chirality is discussed.
Keywords
ChemistryPharmacology, Toxicology and Pharmaceutics
Journal of Medicinal ChemistryAnalysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals
6,241 Citations2014Edon Vitaku, David T. Smith +1 more
NatureThe advent and development of organocatalysis
2,351 Citations2008David W. C. MacMillan
My opinion on why the field of organocatalysis has blossomed so dramatically over the past decade is presented.
Chemical ReviewsComplete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates
2,070 Citations2014Dixit Parmar, Erli Sugiono +2 more
Journal of the American Chemical SocietyEnantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts
1,408 Citations2003Tomotaka Okino, Yasutaka Hoashi +1 more
Michael reaction of malonates to nitrooleolefins with chiral bifunctional organocatalysts, bearing both a thiourea and tertiary amino group, afforded Michael adducts with high yields and enantioselectivities.
Chemical ReviewsAtroposelective Total Synthesis of Axially Chiral Biaryl Natural Products
1,402 Citations2010Gerhard Bringmann, Tanja Gulder +2 more
Gerhard Bringmann's research interests focus on the field of analytical, synthetic, and computational natural product chemistry, i.e., on axially chiral biaryls, which is characterized by a broad structural diversity.
Angewandte Chemie International EditionAtroposelective Synthesis of Axially Chiral Biaryl Compounds
1,379 Citations2005Gerhard Bringmann, Anne J. Price Mortimer +4 more
This Review classifies strategies in the asymmetric synthesis of axially chiral biaryl compounds according to their underlying concepts and critically evaluates their scope and limitations with reference to selected model reactions and applications.
Accounts of Chemical ResearchBINAP: an efficient chiral element for asymmetric catalysis
1,282 Citations1990Ryōji Noyori, Hidemasa Takaya
Chemical Society ReviewsRecent advances and new concepts for the synthesis of axially stereoenriched biaryls
963 Citations2015Joanna Wencel‐Delord, Armen Panossian +2 more
Chemical Society ReviewsTotal synthesis of chiral biaryl natural products by asymmetric biaryl coupling
890 Citations2009Marisa C. Kozlowski, Barbara J. Morgan +1 more
This tutorial review highlights the use of catalytic asymmetric 2-naphthol couplings in total synthesis including nigerone, hypocrellin, calphostin D, phleichrome, and cercosporin.
ChemInformAtroposelective Synthesis of Axially Chiral Biaryl Compounds
864 Citations2005Gerhard Bringmann, Anne J. Price Mortimer +4 more
Journal of Medicinal ChemistryAssessing Atropisomer Axial Chirality in Drug Discovery and Development
839 Citations2011Steven R. LaPlante, Lee D. Fader +6 more
Assessing Atropisomer Axial Chirality in Drug Discovery and Development Steven R. F. Fandrick, Oliver Hucke, Ray Kemper, Stephen P. Miller, and Paul J. Edwards assess the importance of chiral consistency in drug discovery and development.
Angewandte Chemie International EditionThe Challenge of Atropisomerism in Drug Discovery
741 Citations2009Jonathan Clayden, Wesley J. Moran +2 more
This Minireview brings together the various strategies that have been adopted and proposes a general approach to handling an aspect of stereochemistry which has received little attention from drug regulatory agencies.
Natural Product ReportsA twist of nature – the significance of atropisomers in biological systems
602 Citations2015Jamie E. Smyth, Nicholas M. Butler +1 more
The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atrop isomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets.
Chemical ReviewsMetal-Free Multicomponent Syntheses of Pyridines
494 Citations2014Christophe Allais, Jean‐Marie Grassot +2 more
Berichte der deutschen chemischen GesellschaftCondensationsprodukte aus Aldehydammoniak und ketonartigen Verbindungen
468 Citations1881A. Hantzsch
ScienceDynamic Kinetic Resolution of Biaryl Atropisomers via Peptide-Catalyzed Asymmetric Bromination
448 Citations2010Jeffrey L. Gustafson, Daniel Lim +1 more
A tripeptide-derived small-molecule catalyst is presented for the dynamic kinetic resolution of racemic biaryl substrates and a mechanistic model is advanced that accounts for the basis of selectivity observed.
Angewandte ChemieAtropselektive Synthese axial‐chiraler Biaryle
401 Citations2005Gerhard Bringmann, Anne J. Price Mortimer +4 more
Journal of the American Chemical SocietySteric effects. A study of a rationally designed system
376 Citations1980G. BOTT, Leslie D. Field +1 more
Journal of the American Chemical SocietyEnantioselective Synthesis of Multisubstituted Biaryl Skeleton by Chiral Phosphoric Acid Catalyzed Desymmetrization/Kinetic Resolution Sequence
297 Citations2013Keiji Mori, Yūki Ichikawa +4 more
Both experimental and computational studies suggested that this excellent selectivity could be achieved via a highly organized hydrogen bond network among a substrate, a catalyst, and a brominating reagent (N-bromophthalimide).
Journal of the American Chemical SocietyOrganocatalytic Aryl–Aryl Bond Formation: An Atroposelective [3,3]-Rearrangement Approach to BINAM Derivatives
258 Citations2013Gongqiang Li, Hongyin Gao +4 more
Density functional calculations reveal that, in the transition state for C-C bond formation, the phosphoric acid proton of the catalyst is fully transferred to one of the N-atoms of the substrate, and the resulting phosphate acts as a chiral counterion.
Angewandte Chemie International EditionKinetic Resolution of 1,1′‐Biaryl‐2,2′‐Diols and Amino Alcohols through NHC‐Catalyzed Atroposelective Acylation
246 Citations2014Shenci Lu, Si Bei Poh +1 more
A highly efficient NHC-catalyzed kinetic resolution of a wide range of 1,1'-biaryl-2,2'-diols and amino alcohols to provide them in uniformly ≥99% ee represents the first highly enantioselective catalytic acylation of axially chiral alcohols.
Dynamic Stereochemistry of Chiral Compounds: Principles and Applications
222 Citations2008Christian Wolf
ChiralityBiological Stereoselectivity of Atropisomeric Natural Products and Drugs
214 Citations2013Arie Zask, John D. Murphy +1 more
The atropisomeric preference of the receptors and enzyme binding domains makes these agents attractive molecules for drug development in the treatment of various diseases.
Angewandte Chemie International EditionOrganocatalytic Atroposelective Aldol Condensation: Synthesis of Axially Chiral Biaryls by Arene Formation
199 Citations2014Achim Link, Christof Sparr
A synthetic method is demonstrated that efficiently transfers the stereochemical information of a secondary amine organocatalyst into the axial chirality of tri-ortho-substituted biaryls of aromatic polyketides.
Angewandte Chemie International EditionOrganocatalytic Asymmetric Three‐Component Cyclization of Cinnamaldehydes and Primary Amines with 1,3‐Dicarbonyl Compounds: Straightforward Access to Enantiomerically Enriched Dihydropyridines
193 Citations2008Jun Jiang, Jie Yu +3 more
Angewandte Chemie International EditionCatalytic Asymmetric Benzidine Rearrangement
193 Citations2013Chandra Kanta De, Fabio Pesciaioli +1 more
Journal of the American Chemical SocietyEnantioselective Synthesis of Biphenols from 1,4-Diketones by Traceless Central-to-Axial Chirality Exchange
188 Citations2010Fenghai Guo, Leah C. Konkol +1 more
A stereochemical model for this chirality exchange process is put forth on the basis of X-ray crystallographic data, and key to the success of this method is the highly selective transfer of central to axial chorality during a double aromatization event triggered by BF(3)·OEt(2).
Angewandte ChemieAtropisomerie als Herausforderung in der Medikamentenentwicklung
179 Citations2009Jonathan Clayden, Wesley J. Moran +2 more
TetrahedronThe total synthesis of streptonigrin and related antitumor antibiotic natural products
170 Citations2004Gerhard Bringmann, Yanina Reichert +1 more
Angewandte Chemie International EditionCatalytic Enantioselective Synthesis of Atropisomeric Biaryls: A Cation‐Directed Nucleophilic Aromatic Substitution Reaction
148 Citations2014Roly J. Armstrong, Martin D. Smith
A catalytic enantioselective nucleophilic aromatic substitution reaction which yields axially chiral biaryl derivatives in excellent yields with e.r. values of up to 97:3 has been developed, offering access to unexplored chiralBiaryl architectures.
Journal of the American Chemical SocietyBifunctional Organocatalysts for the Enantioselective Synthesis of Axially Chiral Isoquinoline <i>N</i>-Oxides
143 Citations2015Ryota Miyaji, Keisuke Asano +1 more
Angewandte Chemie International EditionFluxionally Chiral DMAP Catalysts: Kinetic Resolution of Axially Chiral Biaryl Compounds
139 Citations2014Gaoyuan Ma, Jun Deng +1 more
Chiral 4-dimethylaminopyridine catalysts with fluxional chirality were found to be efficient in promoting the acylative kinetic resolution of secondary alcohols and axially chiral biaryl compounds with selectivity factors of up to 37 and 51, respectively.
Angewandte Chemie International EditionHighly Enantioselective Kinetic Resolution of Axially Chiral BINAM Derivatives Catalyzed by a Brønsted Acid
134 Citations2014Dao‐Juan Cheng, Liang Yan +7 more
A highly efficient strategy for the kinetic resolution of axially chiral BINAM derivatives involving a chiral Brønsted acid-catalyzed imine formation and transfer hydrogenation cascade process was developed.
Angewandte Chemie International EditionKinetic Resolution of Axially Chiral 2‐Amino‐1,1′‐Biaryls by Phase‐Transfer‐Catalyzed N‐Allylation
132 Citations2013Seiji Shirakawa, Xiangfei Wu +1 more
Examples of catalytic kinetic resolutions of axially chiral amino compounds of type 1 are quite limited, despite the high synthetic utility of these compounds as chiral building blocks for the synthesis of chiral ligands, catalysts, and biologically active compounds.
Journal of the American Chemical SocietyA catalytic method for asymmetric nucleophilic aromatic substitution giving binaphthyls
125 Citations1992Mitsuru Shindo, Kenji Koga +1 more
Chemistry - An Asian JournalOrganocatalyzed Asymmetric Synthesis of Axially, Planar, and Helical Chiral Compounds
118 Citations2015Seiji Shirakawa, Shiyao Liu +1 more
This Focus Review summarizes asymmetric organocatalytic methods for the synthesis of axially, planar, and helical chiral compounds as useful chiral building blocks.
SynlettOrganocatalytic Strategies for the Synthesis of Axially Chiral Compounds
104 Citations2015Giorgio Bencivenni
MoleculesSynthesis and Aromatization of Hantzsch 1,4-Dihydropyridines under Microwave Irradiation. An Overview
98 Citations2003Jean Jacques Vanden Eynde, Annie Mayence
Journal of the American Chemical SocietyThe complete intramolecular transfer of a central chiral element to an axial chiral element. Oxidation of (S)-4-naphthyldihydroquinolines to (S)-4-naphthylquinolines
94 Citations1984A. I. MEYERS, David G. Wettlaufer
Chemical ScienceN-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes
90 Citations2015Lisa Candish, Alison Levens +1 more
N-Heterocyclic carbene catalysed redox isomerisation with reduction about the carbonyl has been developed in the transformation of trienyl esters to tetrasubstituted benzaldehydes.
SynthesisEnantioselective Organocatalyzed Domino Synthesis of Six-Membered Carbocycles
89 Citations2013Damien Bonne, Jean Rodríguez +4 more
Journal of the American Chemical SocietyChirality Exchange from sp<sup>3</sup> Central Chirality to Axial Chirality: Benzannulation of Optically Active Diaryl-2,2-dichlorocyclopropylmethanols to Axially Chiral α-Arylnaphthalenes
87 Citations2004Yoshinori Nishii, Kazunori Wakasugi +2 more
Chirality exchange benzannulation of optically active (1S)-aryl(aryl')-2,2-dichlorocyclopropylmethanols using TiCl4 successfully proceeded to give axially chiral (M)-alpha-arylnaphthalenes with excellent levels of stereo induction.
Chemistry - An Asian JournalOrganocatalytic Enantioselective One‐Pot Synthesis and Application of Substituted 1,4‐Dihydropyridines—Hantzsch Ester Analogues
86 Citations2007Patrick T. Franke, Rasmus Lyng Johansen +2 more
The one-pot reaction of alpha,beta-unsaturated aldehydes with beta-diketones or beta-ketoesters and primary amines gives optically active 2,3-substituted 1,4-dihydropyridines in moderate yields and with enantioselectivities up to 95 % ee.
Angewandte ChemieKinetic Resolution of 1,1′‐Biaryl‐2,2′‐Diols and Amino Alcohols through NHC‐Catalyzed Atroposelective Acylation
85 Citations2014Shenci Lu, Si Bei Poh +1 more
Chemical CommunicationsMetal-free Michael addition initiated multicomponent oxidative cyclodehydration route to polysubstituted pyridines from 1,3-dicarbonyls
84 Citations2008Frédéric Liéby‐Muller, Christophe Allais +2 more
A simple metal-free, step-economic and selective access to pyridines from readily available substrates is reported, involving a flexible 4 A molecular sieves promoted Michael addition initiated domino three-component reaction between a 1,3-dicarbonyl, a Michael acceptor and a synthetic equivalent of ammonia.
Angewandte ChemieOrganokatalytische atropselektive Aldolkondensation: Synthese axial‐chiraler Biaryle durch Arenbildung
79 Citations2014Achim Link, Christof Sparr
Angewandte Chemie International EditionPalladium‐Catalyzed Enantioselective Intramolecular Hydroarylation of Alkynes To Form Axially Chiral 4‐Aryl 2‐Quinolinones
78 Citations2011Tetsuro Shibuya, Yu Shibata +2 more
The Journal of Organic ChemistryTotal Synthesis of the Antitumor Antibiotic (±)-Streptonigrin: First- and Second-Generation Routes for de Novo Pyridine Formation Using Ring-Closing Metathesis
70 Citations2013Timothy J. Donohoe, Christopher R. Jones +7 more
Assessment of a number of chiral ligands in a challenging asymmetric Suzuki–Miyaura cross-coupling reaction has enabled enantioenriched (up to 42% ee) synthetic streptonigrin intermediates to be prepared for the first time.
Angewandte Chemie International EditionEnantioselective Total Synthesis and Studies into the Configurational Stability of Bismurrayaquinone A
68 Citations2011Leah C. Konkol, Fenghai Guo +2 more
The concise strategy of the first enantioselective total synthesis of bismurrayaquinone A utilized traceless stereochemical exchange to form an enantioenriched biphenyl core that was elaborated in a bidirectional manner to the natural product.
Tetrahedron LettersHighly stereospecific conversion of C-centrochirality of a 3,4-dihydro-2H-1,1′-binaphthalen-1-ol into axial chirality of a 3,4-dihydro-1,1′-binaphthalene
66 Citations2001Tetsutaro Hattori, Masamitsu Date +4 more
Angewandte Chemie International EditionConcise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor
63 Citations2015Keith R. Fandrick, Wenjie Li +23 more
The combination of a copper-catalyzed acylation along with the implementation of the BI-DIME ligands for a ligand-controlled Suzuki cross-coupling and an unprecedented bis(trifluoromethane)sulfonamide-Catalyzed tert-butylation renders the synthesis of this complex molecule robust, safe, and economical.
Angewandte Chemie International EditionSynthesis of Atropisomerically Defined, Highly Substituted Biaryl Scaffolds through Catalytic Enantioselective Bromination and Regioselective Cross‐Coupling
61 Citations2011Jeffrey L. Gustafson, Daniel Lim +2 more
The preparation of single atropisomer scaffolds could lead to increases in potency for small molecules, through an increase in the effective concentration of the biologically active atrop isomer, with the exclusion of a less active, or alternatively active form.
Angewandte ChemieCatalytic Enantioselective Synthesis of Atropisomeric Biaryls: A Cation‐Directed Nucleophilic Aromatic Substitution Reaction
58 Citations2014Roly J. Armstrong, Martin D. Smith
Chemical ReviewsEnantioselectively-Catalyzed Reactions with (<i>E</i>)-2-Alkenoyl-pyridines, Their<i>N</i>-Oxides, and the Corresponding Chalcones
58 Citations2014Giovanni Desimoni, Giuseppe Faita +1 more
Tetrahedron LettersMetal-free Brønsted acids catalyzed synthesis of functional 1,4-dihydropyridines
56 Citations2007J. MOREAU, Agathe Duboc +3 more
The Journal of Organic ChemistryAtropisomerism in the 2-Arylimino-<i>N</i>-(2-hydroxyphenyl)thiazoline Series: Influence of Hydrogen Bonding on the Racemization Process
54 Citations2007Christian Roussel, Nicolas Vanthuyne +4 more
A series of original atropisomeric iminothiazolines 1 in which X = OH or (and) Y = OH were prepared from the corresponding methoxy precursors, and the barriers to enantiomerization are given.
Chemistry - A European Journal<i>B</i> Values as a Sensitive Measure of Steric Effects
53 Citations2009Renzo Ruzziconi, Sara Spizzichino +3 more
Torsional barriers of 15 ortho-substituted biphenyls have been determined computationally using the B3LYP density functional and experimentally by variable-temperature ("dynamic") nuclear magnetic resonance.
Angewandte ChemieHighly Enantioselective Kinetic Resolution of Axially Chiral BINAM Derivatives Catalyzed by a Brønsted Acid
52 Citations2014Dao‐Juan Cheng, Liang Yan +7 more
Angewandte ChemieOrganocatalytic Asymmetric Three‐Component Cyclization of Cinnamaldehydes and Primary Amines with 1,3‐Dicarbonyl Compounds: Straightforward Access to Enantiomerically Enriched Dihydropyridines
48 Citations2008Jun Jiang, Jie Yu +3 more
Chemical SciencePrediction of suitable catalyst by 1H NMR: asymmetric synthesis of multisubstituted biaryls by chiral phosphoric acid catalyzed asymmetric bromination
47 Citations2013Keiji Mori, Yūki Ichikawa +4 more
Based on this method, multisubstituted biaryls that occur frequently in many biologically active compounds, chiral ligands, and organocatalysts, with excellent enantioselectivities via chiral phosphoric acid-catalyzed asymmetric bromination are constructed.
Journal of the American Chemical SocietyStudies on Dihydropyridines. III. An Absolute Asymmetric Synthesis and an Attempted Conversion of Carbon Atom Asymmetry to Biphenyl Asymmetry<sup>1</sup>
46 Citations1955Jerome A. Berson, Earlene Brown
Angewandte ChemieFluxionally Chiral DMAP Catalysts: Kinetic Resolution of Axially Chiral Biaryl Compounds
41 Citations2014Gaoyuan Ma, Jun Deng +1 more
Angewandte ChemieConcise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor
40 Citations2015Keith R. Fandrick, Wenjie Li +23 more
Angewandte Chemie International EditionEnantioselective Organocatalytic Multicomponent Synthesis of 2,6‐Diazabicyclo[2.2.2]octanones
37 Citations2013Maria del Mar Sanchez Duque, Olivier Baslé +5 more
The title reaction of β-ketoamides, acrolein, and aminophenols, catalyzed by a bifunctional thiourea-tertiary amine organocatalyst, enables the preparation of an enantioenriched diazabicyclo (2,6-DABCO) scaffold with excellent yields and high levels of stereocontrol.
Angewandte Chemie International Edition in EnglishInversion of Optically Active Dihydropyridines by Oxidation and Electroreduction
37 Citations1996Alexander Straub, Axel Goehrt
Letters in Organic ChemistrySynthesis, Chiral Separation, Barrier to Rotation and Absolute Configuration of N-(O- Functionalized-Aryl)-4-Alkyl-Thiazolin-2-One and Thiazoline-2-Thione Atropisomers
33 Citations2005Nicolas Vanthuyne, Federico Andreoli +3 more
Current Organic ChemistryMichael Addition-initiated Sequential Reactions from 1,3-dicarbonyls for the Synthesis of Polycyclic Heterocycles
32 Citations2013Xavier Bugaut, Damien Bonne +3 more
Current Organic ChemistryNew Approaches to Nitrogen Containing Heterocycles: Enantioselective Organocatalyzed Synthesis of Dihydropyridines (DHP's), Quinolizidine Derivatives and Dihydropyrimidines (DHPM's)
31 Citations2012Hoai T. B. Pham, Isabelle Chataigner +1 more
Tetrahedron LettersBifunctional chiral urea catalyzed highly enantioselective Michael addition of cyclic 1,3-dicarbonyl compounds to 2-enoylpyridines
30 Citations2013Nagaraju Molleti, S. Allu +2 more
This asymmetric methodology could afford both enantiomers of the products with the same level of enantioselectivities by using pseudoenantiomeric catalysts with up to 98% ee and in excellent yields.
Catalysis Science & TechnologyIn-depth structure–selectivity investigations on asymmetric, copper-catalyzed oxidative biaryl coupling in the presence of 5-cis-substituted prolinamines
29 Citations2015Felix Prause, Benjamin Arensmeyer +2 more
Angewandte ChemieEnantioselective Total Synthesis and Studies into the Configurational Stability of Bismurrayaquinone A
26 Citations2011Leah C. Konkol, Fenghai Guo +2 more
Advanced Synthesis & CatalysisOrganocatalytic Enantioselective Multicomponent Synthesis of Pyrrolopiperazines
25 Citations2014Haiying Du, Jean Rodríguez +2 more
Substantial possibilities for variation on the three reaction partners [β-keto ester, enal and N-(2-aminoethyl)pyrrole] along with excellent enantioselectivities are the highlights of the present transformation.
Organic LettersAn Efficient One-Pot Asymmetric Synthesis of Biaryl Compounds via Diels−Alder/Retro-Diels−Alder Cascade Reactions
23 Citations2007Yongxiang Liu, Kui Lu +6 more
A single-step chirality transfer method for the synthesis of axially chiral biaryl compounds by construction of the second aromatic ring via a Diels-Alder/retro-Diels- alder cascade reaction is reported.
Chemical CommunicationsOrganocatalytic multicomponent synthesis of enantioenriched polycyclic 1,2,3,4-tetrahydropyridines: key substrate selection enabling regio- and stereoselectivities
20 Citations2014Yohan Dudognon, Haiying Du +3 more
The key to the success of this reaction was the use of polyfunctional substrates including 2-aminophenols and scarcely used β-ketoamides triggering a thermodynamically controlled regio- and diastereoselective sequence.
Chemical CommunicationsSynthesis of unsymmetrically substituted 2,2′-dihydroxy-1,1′-biaryl derivatives using organic-base-catalyzed Ferrier-type rearrangement as the key step
18 Citations2012Masahiro Terada, Katsunori Dan
A strong organic base, TBD, functioned as a unique catalyst for the intramolecular multi-step transformation of lactols using the Ferrier-type rearrangement as the key step to provide unsymmetrically substituted 2,2'-dihydroxy biaryl compounds having four ortho substituents about the biaryl axis without the need for a metal catalyst.
Angewandte ChemieSynthesis of Atropisomerically Defined, Highly Substituted Biaryl Scaffolds through Catalytic Enantioselective Bromination and Regioselective Cross‐Coupling
17 Citations2011Jeffrey L. Gustafson, Daniel Lim +2 more
Angewandte ChemiePalladium‐Catalyzed Enantioselective Intramolecular Hydroarylation of Alkynes To Form Axially Chiral 4‐Aryl 2‐Quinolinones
17 Citations2011Tetsuro Shibuya, Yu Shibata +2 more
Angewandte ChemieInversion optisch aktiver Dihydropyridine durch Oxidation und Elektroreduktion
15 Citations1996Alexander Straub, Axel Goehrt
Angewandte ChemieEnantioselektiver Aufbau polyaromatischer Architekturen durch Organokatalyse
14 Citations2014Ophélie Quinonero, Cyril Bressy +1 more
Angewandte ChemieEnantioselective Organocatalytic Multicomponent Synthesis of 2,6‐Diazabicyclo[2.2.2]octanones
11 Citations2013Maria del Mar Sanchez Duque, Olivier Baslé +5 more
…