Organocatalytic Enantioselective Friedel−Crafts Reactions of 1-Naphthols with Aldimines
Organic LettersPublished 14 January 2011
Guixia Liu, Shilei Zhang, Hao Li, Tang‐Zhi Zhang, Wei Wang
Citations77
SJR quartileQ1
SJR score1.24
SNIP1.03
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
An organocatalytic enantioselective Friedel-Crafts reaction of 1-naphthols with aldimines has been developed and affords a direct access to chiral aminoarylnaphthol in good yields and with good to high enantiOSElectivities.
Abstract
An organocatalytic enantioselective Friedel-Crafts reaction of 1-naphthols with aldimines has been developed. The method affords a direct access to chiral aminoarylnaphthols in good yields and with good to high enantioselectivities.
Keywords
Chemistry
Chemical ReviewsSmall-Molecule H-Bond Donors in Asymmetric Catalysis
2,574 Citations2007Abigail G. Doyle, Eric N. Jacobsen
Angewandte Chemie International EditionAsymmetric Catalysis by Chiral Hydrogen‐Bond Donors
1,900 Citations2006Mark S. Taylor, Eric N. Jacobsen
This review documents the structural and mechanistic features that contribute to high enantioselectivity in hydrogen-bond-mediated catalytic processes in small-molecule, synthetic catalyst systems.
Angewandte Chemie International EditionCatalytic Functionalization of Indoles in a New Dimension
1,421 Citations2009Marco Bandini, Astrid Eichholzer
This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.
Chemical Society ReviewsMetal-free organocatalysis through explicit hydrogen bonding interactions
1,251 Citations2003Peter R. Schreiner
This field is briefly reviewed here, along with some rough guidelines and concepts for further catalyst development, which offers attractive alternatives to metal (ion)-catalyzed reactions by combining supramolecular recognition with chemical transformations in an environmentally benign fashion.
Chemical Society Reviews(Thio)urea organocatalysis—What can be learnt from anion recognition?
1,093 Citations2009Zhiguo Zhang, Peter R. Schreiner
The present critical review outlines the close relationship and mutual interplay between molecular recognition, active site considerations in enzyme catalysis involving anions, and organocatalysis utilizing explicit hydrogen bonding.
Organic LettersHighly Enantioselective Conjugate Addition of Nitromethane to Chalcones Using Bifunctional Cinchona Organocatalysts
979 Citations2005Benedek Vakulya, Szilárd Varga +2 more
Cinchona alkaloid-derived chiral bifunctional thiourea organocatalysts were synthesized and applied in the Michael addition between nitromethane and chalcones with high ee and chemical yields.
Advanced Synthesis & CatalysisRecent Progress in Chiral Brønsted Acid Catalysis
888 Citations2006Takahiko Akiyama, Junji Itoh +1 more
Chemistry - A European JournalOrganocatalysis Mediated by (Thio)urea Derivatives
839 Citations2006Stephen J. Connon
The development of N,N-dialkyl(thio)urea derivatives is charted, from early "proof-of-concept" materials to contemporary active chiral (bifunctional) promoters of highly selective asymmetric transformations.
ChemInformHighly Enantioselective Conjugate Addition of Nitromethane to Chalcones Using Bifunctional Cinchona Organocatalysts.
816 Citations2005Benedek Vakulya, Szilárd Varga +2 more
Organic & Biomolecular ChemistryRecognition and activation by ureas and thioureas: stereoselective reactions using ureas and thioureas as hydrogen-bonding donors
761 Citations2005Yoshiji Takemoto
Enantioselective reactions catalyzed by urea and thiourea derivatives as general acid catalysts as well as diastereoselectives reactions are described.
Chemical Society ReviewsChiral Brønsted acid catalyzed Friedel–Crafts alkylation reactions
757 Citations2009Shu‐Li You, Quan Cai +1 more
In this tutorial review, recent progress in the development of chiral Brønsted acid-catalyzed asymmetric Friedel-Crafts reactions is presented.
Chemical ReviewsCatalytic Asymmetric Friedel−Crafts Alkylation Reactions—Copper Showed the Way
757 Citations2008Thomas B. Poulsen, Karl Anker Jørgensen
Alkylation with Activated Alkenes and Carbonyl Compounds in Copper Complexes and Other Metal Complexes: The Incubation Period 2904-2904 3.2.1.
Beilstein Journal of Organic ChemistryA review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis
659 Citations2010Magnus Rueping, Boris J. Nachtsheim
The new catalytic approaches described in this review are favoured over classical Friedel–Crafts conditions as benzyl-, propargyl- and allyl alcohols, or styrenes, can be used instead of toxic benzyl halides and only low catalyst loadings are needed to provide a wide range of products.
Chemical ReviewsAsymmetric Catalysis Mediated by Synthetic Peptides
641 Citations2007Elizabeth A. Colby Davie, Steven M. Mennen +2 more
Accounts of Chemical ResearchAsymmetric Organic Catalysis with Modified Cinchona Alkaloids
618 Citations2004Shi‐Kai Tian, Yonggang Chen +4 more
These studies demonstrate the potential of modified cinchona alkaloids as broadly useful chiral organic catalysts for asymmetric synthesis.
Journal of the American Chemical SocietyHighly Enantioselective Conjugate Addition of Malonate and β-Ketoester to Nitroalkenes: Asymmetric C−C Bond Formation with New Bifunctional Organic Catalysts Based on Cinchona Alkaloids
526 Citations2004Hongming Li, Yi Wang +2 more
The development of a new class of readily accessible chiral bifunctional organic catalysts that could be derived in one or two steps in high yield from either quinidine or quinine are described.
ScienceAsymmetric Cooperative Catalysis of Strong Brønsted Acid–Promoted Reactions Using Chiral Ureas
495 Citations2010Hao Xu, Stephan J. Zuend +3 more
A strategy for inducing enantioselectivity in reactions of protio-iminium ions, wherein a chiral catalyst interacts with the highly reactive intermediate through a network of noncovalent interactions, which leads to an attenuation of the reactivity of the iminium ion and allows high enantioinduction in cycloadditions with electron-rich alkenes.
Organic & Biomolecular ChemistryOrganocatalysis: asymmetric cascade reactions catalysed by chiral secondary amines
482 Citations2008Xinhong Yu, Wei Wang
These powerful synthetic methodologies serve as efficient approaches to the construction of complex chiral molecular architectures from simple achiral materials in one-pot transformations under mild conditions with high stereocontrol.
Journal of the American Chemical SocietyHighly Enantioselective Friedel−Crafts Reaction of Indoles with Imines by a Chiral Phosphoric Acid
406 Citations2007Qiang Kang, Zhuo‐An Zhao +1 more
Highly enantioselective Friedel−Crafts reactions of indoles with imines catalyzed by a chiral phosphoric acid are developed, affording the 3-indolyl methanamine derivatives with up to >99% ee for a wide range of substrates.
Angewandte Chemie International EditionStereocontrolled Creation of Adjacent Quaternary and Tertiary Stereocenters by a Catalytic Conjugate Addition
399 Citations2004Hongming Li, Yi Wang +6 more
Journal of the American Chemical SocietyOrganocatalytic Asymmetric Aza-Friedel−Crafts Alkylation of Furan
353 Citations2004Daisuke Uraguchi, Keiichi Sorimachi +1 more
The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion and could be further derivatized to a chiral gamma-butenolid.
Angewandte Chemie International EditionCupreines and Cupreidines: An Emerging Class of Bifunctional Cinchona Organocatalysts
351 Citations2006Tommaso Marcelli, Jan H. van Maarseveen +1 more
The scope and modes of action of this new class of asymmetric bifunctional organocatalysts based on cinchona alkaloids, which feature a phenolic OH group in the C6' position, are described.
Journal of the American Chemical SocietyEnantioselective Friedel−Crafts Reaction of Electron-Rich Alkenes Catalyzed by Chiral Brønsted Acid
331 Citations2006Masahiro Terada, Keiichi Sorimachi
The reaction of various indole derivatives with a broad range of substituted enecarbamates affords the corresponding Friedel−Crafts products in high yield and enantioselectivity.
Angewandte Chemie International EditionChiral Brønsted Acid Catalyzed Enantioselective Friedel–Crafts Reaction of Indoles and α‐Aryl Enamides: Construction of Quaternary Carbon Atoms
321 Citations2007Yi‐Xia Jia, Jun Zhong +3 more
Hydrogen Bonding in Organic Synthesis
319 Citations2009
Journal of the American Chemical SocietyAsymmetric Friedel−Crafts Reaction of Indoles with Imines by an Organic Catalyst
305 Citations2006Yong‐Qiang Wang, Jun Tae Song +3 more
This is the first efficient organocatalytic asymmetric Friedel-Crafts reaction of indoles with imines catalyzed by a bifunctional cinchona alkaloid catalyst, establishing a direct, convergent, and versatile approach to optically active 3-indolyl methanamines, a structural motif embedded in numerous indole alkaloids and synthetic indole derivatives.
European Journal of Organic ChemistryOrganocatalyzed Asymmetric Friedel–Crafts Reactions
284 Citations2010Vincent Terrasson, Renata Marcia de Figueiredo +1 more
Angewandte Chemie International EditionChirally Aminated 2‐Naphthols—Organocatalytic Synthesis of Non‐Biaryl Atropisomers by Asymmetric Friedel–Crafts Amination
248 Citations2006Sebastian Brandes, Marco Bella +2 more
Organic LettersChiral Binaphthyl-Derived Amine-Thiourea Organocatalyst-Promoted Asymmetric Morita−Baylis−Hillman Reaction
234 Citations2005Jian Wang, Hao Li +3 more
A new bifunctional binaphthyl-derived amine thiourea organocatalyst has been developed to promote enantioselective Morita-Baylis-Hillman reaction of cyclohexenone with a wide range of aldehydes.
Organic LettersOrganocatalytic Asymmetric Michael Addition of 2,4-Pentandione to Nitroolefins
224 Citations2005Jian Wang, Hao Li +3 more
A novel binaphthyl-derived amine thiourea organocatalyst has been developed and demonstrated to efficiently catalyze Michael addition reactions (using as low as 1 mol % loading) of diketones to nitroalkenes with remarkably high enantioselectivities.
ChemInformOrganocatalytic Asymmetric Michael Addition of 2,4‐Pentandione to Nitroolefins.
191 Citations2006Jian Wang, Hao Li +3 more
Organic LettersThe Highly Enantioselective Addition of Indoles to <i>N</i>-Acyl Imines with Use of a Chiral Phosphoric Acid Catalyst
190 Citations2007Gerald B. Rowland, Emily B. Rowland +3 more
The highly enantioselective organocatalytic addition of N-benzyl indoles to N-acyl imines is reported and attractive features of the reaction include desirable catalyst loadings, good reactivity, generality of substrates, and easily removable groups from both nitrogen atoms.
Catalytic Asymmetric Friedel–Crafts Alkylations
177 Citations2009Marco Bandini, Achille Umani‐Ronchi
Chemistry - A European JournalHighly Enantioselective Friedel–Crafts Reaction of 4,7‐Dihydroindoles with Imines by Chiral Phosphoric Acids: Facile Access to 2‐Indolyl Methanamine Derivatives
156 Citations2008Qiang Kang, Xiaojian Zheng +1 more
Advanced Synthesis & CatalysisChiral Phosphoric Acid‐Catalyzed Enantioselective Aza‐Friedel–Crafts Reaction of Indoles
155 Citations2007Masahiro Terada, Shigeko Yokoyama +2 more
Organic LettersOrganocatalytic Enantioselective Friedel−Crafts Reaction of Pyrrole Derivatives with Imines
152 Citations2007Guilong Li, Gerald B. Rowland +2 more
A highly enantioselective Friedel-Crafts reaction of pyrrole derivatives with N-acyl imines catalyzed by chiral phosphoric acids was developed and produced the pyr role derivatives in high yields and enantiOSElectivity.
Chemical CommunicationsAn enantioselective synthesis of heteroaromatic N-tosyl α-amino acids
137 Citations1999Mogens Johannsen
A new synthesis of optically active β-indolyl and pyrrolyl N-tosyl α-amino acids has been developed which uses readily available starting materials and proceeds with a high degree of enantioselection, giving up to 96% enantiomeric purity in 89% yield using 1–5 mol% of a chiral copper(I)–Tol-BINAP catalyst.
Chemical CommunicationsOrganocatalytic asymmetric Friedel–Crafts alkylation/cascade reactions of naphthols and nitroolefins
135 Citations2007Tianyu Liu, Hai‐Lei Cui +6 more
The asymmetric Michael-type Friedel-Crafts reaction of naphthols and nitroolefins promoted by bifunctional thiourea-tertiary amine organocatalysts was investigated, finding that further cascade reactions could occur to generate enantiopure dimeric tricyclic 1,2-dihydronaphtho[2,1-b]furanyl-2-hydroxylamine derivatives.
The Journal of Organic ChemistrySolvent-Free Asymmetric Aminoalkylation of Electron-Rich Aromatic Compounds: Stereoselective Synthesis of Aminoalkylnaphthols by Crystallization-Induced Asymmetric Transformation
127 Citations2001Cristina Cimarelli, Andrea Mazzanti +2 more
Electron-rich aromatic compounds such as 2-naphthol give a faster and asymmetric 1-aminoalkylation with high yields when treated with (R)-1-phenylethylamine and aromatic aldehydes in solvent-free conditions.
Advanced Synthesis & CatalysisChiral Brønsted Acid‐Mediated Enantioselective Organocatalytic Three‐Component Reaction for the Construction of Trifluoromethyl‐Containing Molecules
121 Citations2008Guangwu Zhang, Lian Wang +2 more
Current Organic SynthesisSyntheses and Transformations of 1-(&#945;-Aminobenzyl)-2-Naphthol Derivatives
119 Citations2004István Szatmári, Ferenc Fülöp
Angewandte Chemie International Edition in EnglishEnantioselective Catalysis with a New Zirconium Trichloride Lewis Acid Containing a “Dibornacyclopentadienyl” Ligand
114 Citations1990Gerhard Erker, A. A. H. VAN DER ZEIJDEN
The Journal of Organic ChemistryNonracemic Betti Base as a New Chiral Auxiliary: Application to Total Syntheses of Enantiopure (2<i>S</i>,6<i>R</i>)-Dihydropinidine and (2<i>S</i>,6<i>R</i>)-Isosolenopsins
110 Citations2005Xinyan Wang, Yanmei Dong +4 more
(S)-Betti base was proved to be an excellent chiral auxiliary and a novel Pd/C catalyzed N-debenzylation straightforward to amine hydrochloride was developed in the presence of CH2Cl2.
Organic LettersThe Application of Chiral Aminonaphthols in the Enantioselective Addition of Diethylzinc to Aryl Aldehydes
107 Citations2001Daxue Liu, Licheng Zhang +6 more
The Journal of Organic ChemistryA Convenient, One-Step Synthesis of Optically Active Tertiary Aminonaphthol and Its Applications in the Highly Enantioselective Alkenylations of Aldehydes
106 Citations2003Jian‐Xin Ji, Liqin Qiu +2 more
Optically active tertiary aminonaphthol 1 was obtained by a new, convenient procedure and was found to catalyze the enantioselective alkenylation of various aldehydes with high ee values, which provides a practical method for the synthesis of chiral (E)- allyl alcohols.
The Journal of Organic ChemistryOrganocatalytic Asymmetric Friedel−Crafts Alkylation/Cyclization Cascade Reaction of 1-Naphthols and α,β-Unsaturated Aldehydes: An Enantioselective Synthesis of Chromanes and Dihydrobenzopyranes
106 Citations2009Liang Hong, Lei Wang +3 more
An enantioselective Friedel-Crafts alkylation/cyclization cascade reaction of 1-naphthols and alpha,beta-unsaturated aldehydes promoted by diphenylprolinol ether has been developed and a plausible mechanism has been proposed to explain the origin of the activation and the asymmetric induction.
The Journal of Organic ChemistryAsymmetric Catalysis of the Friedel−Crafts Reaction with Fluoral by Chiral Binaphthol-Derived Titanium Catalysts through Asymmetric Activation
105 Citations2000Akihiro Ishii, Vadim A. Soloshonok +1 more
Chemical Communications9-Thiourea Cinchona alkaloid supported on mesoporous silica as a highly enantioselective, recyclable heterogeneous asymmetric catalyst
98 Citations2008Yu Peng, Jing He +1 more
A readily recycled and regenerated heterogeneous catalyst of 9-thiourea epi-quinine supported on mesoporous silica exhibits enhanced enantioselectivity in the asymmetric Friedel-Crafts reaction of imines with indoles.
Journal of Heterocyclic ChemistryTransformation reactions of the betti base analog aminonaphthols
84 Citations2004István Szatmári, Anasztázia Hetényi +2 more
Tetrahedron AsymmetryA practical stereoselective synthesis of secondary and tertiary aminonaphthols: chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde
79 Citations2002Cristina Cimarelli, Gianni Palmieri +1 more
Advanced Synthesis & CatalysisEnantioselective Organocatalytic Synthesis of Arylglycines <i>via</i> Friedel–Crafts Alkylation of Arenes with a Glyoxylate Imine
79 Citations2010Dieter Enders, Matthias Seppelt +1 more
The enantioselectiveOrganocatalytic synthesis of arylglycines has been developed employing 1 mol% of an enantiopure N-triflyl phosphoramide Bronsted acid as organocatalyst and a novel protocol for the deprotection of the N-tert-butylsulfonyl (Bus) group is developed.
Journal of the American Chemical SocietyEnantioselective Preparation of a Stable Boronate Complex Stereogenic Only at Boron
69 Citations2008Peter F. Kaiser, Jonathan M. White +1 more
The boronate complex is formed with >99% ee and is remarkably configurationally stable, with no racemization observed after 24 h at 110°.
The Journal of Organic ChemistryAn Efficient Kinetic Resolution of Racemic Betti Base Based on an Enantioselective <b><i>N</i></b>,<b><i>O</i></b>-Deketalization
63 Citations2005Yanmei Dong, Rui Li +4 more
An efficient kinetic resolution of racemic Betti base with L-(+)-tartaric acid in acetone was developed based on a novel enantioselective N,O-deketalization, in excellent yields with a practically foolproof operation.
MoleculesSynthesis of New 1,3-Disubstituted-2,3-dihydro-1H-naphth[1,2e][1,3]oxazines
57 Citations2007Zuhal Turgut, Emel Pelit +1 more
1, 3-Disubstituted-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazines were prepared through the ring-closure reactions of the aminobenzylnaphTHols with substituted aryl- and heteroarylaldehydes.
Organic LettersSynthesis of Chiral Vicinal Diamines by Highly Diastereoselective Three-Component Phenolic Mannich Reaction: Temperature-Dependent Stereodivergency
50 Citations2005Christophe Rondot, Jieping Zhu
A diastereoselective three-component synthesis of chiral o-1,2-diaminoalkyl phenols from an electron-rich phenol, an amine, and a chiral alpha-N,N-dibenzylamino aldehyde is developed.
European Journal of Organic ChemistrySynthesis of 2,4‐Diaryl‐3,4‐dihydro‐2<i>H</i><b>‐</b>naphth[2,1‐<i>e</i>][1,3]oxazines and Study of the Effects of the Substituents on Their Ring<i>‐</i>Chain Tautomerism
44 Citations2004István Szatmári, Tamás A. Martinek +2 more
Tetrahedron AsymmetryHighly diastereoselective aminoalkylation of naphthols with chiral amines mediated by lithium perchlorate solution in diethyl ether
42 Citations2003Mohammad R. Saidi, Najmedin Azizi
Tetrahedron AsymmetryDiastereoselective Friedel–Crafts reaction of α-trifluoromethyl imines derived from chiral amines
40 Citations2001Yuefa Gong, Katsuya Kato
Tetrahedron AsymmetryHighly regioselective N-alkylation of nonracemic Betti base: a novel one-pot synthesis of chiral N-methyl-N-alkyl Betti bases
40 Citations2004Yanmei Dong, Jianwei Sun +4 more
ChromatographiaHPLC Enantioseparation of 1-(α-Aminobenzyl)-2-naphthol and 2-(α-Aminobenzyl)-1-naphthol Analogs on a β-Cyclodextrin-Based Chiral Stationary Phase
16 Citations2007Róbert Berkecz, István Ilisz +5 more
