Complex Bioactive Alkaloid‐Type Polycycles through Efficient Catalytic Asymmetric Multicomponent Aza‐Diels–Alder Reaction of Indoles with Oxetane as Directing Group
Angewandte Chemie International EditionPublished 9 January 2013
Zhilong Chen, Beilei Wang, Zhaobin Wang, Guangyu Zhu, Jianwei Sun
Citations213
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.
Abstract
Starting from three achiral compounds, the title reaction provides rapid access to a variety of molecules that contain indoline, tetrahydroquinoline, and tetrahydroisoquinoline moieties (see scheme). The process features the efficient formation of multiple new bonds and chiral centers, excellent stereoselectivity, oxetane desymmetrization, and easy product purification through filtration.
Keywords
Chemistry
ScienceDrug Discovery and Natural Products: End of an Era or an Endless Frontier?
2,054 Citations2009Jesse W.-H. Li, John C. Vederas
Untapped biological resources, “smart screening” methods, robotic separation with structural analysis, metabolic engineering, and synthetic biology offer exciting technologies for new natural product drug discovery.
Angewandte Chemie International EditionAsymmetric Multicomponent Reactions (AMCRs): The New Frontier
1,664 Citations2005Diego J. Ramón, Miguel Yus
Asymmetric multicomponent reactions involve the preparation of chiral compounds by the reaction of three or more reagents added simultaneously and has some advantages over classic divergent reaction strategies, such as lower costs, time, and energy, as well as environmentally friendlier aspects.
Chemical ReviewsCatalytic Enantioselective Addition to Imines
1,564 Citations1999Shū Kobayashi, Haruro Ishitani
Shū Kobayashi was born in 1959 in Tokyo, Japan and studied chemistry at the University of Tokyo and received his Ph.D. in 1988 (Professor T. Mukaiyama), and received the first Springer Award in Organometallic Chemistry in 1997.
Chemical ReviewsSubstrate-directable chemical reactions
1,468 Citations1993Amir H. Hoveyda, David A. Evans +1 more
SynthesisChiral Phosphoric Acids as Versatile Catalysts for Enantioselective Transformations
1,254 Citations2010Masahiro Terada
Chemical ReviewsChemistry and Biology of the Tetrahydroisoquinoline Antitumor Antibiotics
1,136 Citations2002Jack D. Scott, Robert M. Williams
Chemical CommunicationsBinaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon–carbon bond forming reactions
1,025 Citations2008Masahiro Terada
Binaphthol-derived monophosphoric acids have been designed as novel chiral Brønsted-acid catalysts, which function as efficient enantioselective catalysts for a variety of organic transformations, especially for carbon-carbon bond forming reactions.
Accounts of Chemical ResearchBrønsted-Acid-Catalyzed Asymmetric Multicomponent Reactions for the Facile Synthesis of Highly Enantioenriched Structurally Diverse Nitrogenous Heterocycles
896 Citations2011Jie Yu, Feng Shi +1 more
A detailed investigation of several MCRs catalyzed by chiral phosphoric acids that lead to the production of structurally diverse nitrogenous heterocycles is presented, including Biginelli and Biginelli-like reactions; 1,3-dipolar cycloadditions; aza Diels-Alder reactions; and some other cyclization reactions.
Advanced Synthesis & CatalysisRecent Progress in Chiral Brønsted Acid Catalysis
888 Citations2006Takahiko Akiyama, Junji Itoh +1 more
Chemical Society ReviewsRecent developments in asymmetric multicomponent reactions
854 Citations2012Corien de Graaff, Eelco Ruijter +1 more
Significantly broadened scopes, new techniques, more environmentally benign methods and entirely novel MCRs reflect the increasingly inventive paths that synthetic chemist follow in this field of asymmetric multicomponent reactions.
Angewandte Chemie International EditionNonlinear Effects in Asymmetric Synthesis and Stereoselective Reactions: Ten Years of Investigation
836 Citations1998Christian Girard, Henri B. Kagan
Nonlinear effects of an enantiomerically impure catalyst on an asymmetric synthesis are not only of academic interest since they have a variety of practical uses, which are highlighted in this review.
Proceedings of the National Academy of SciencesAttractive noncovalent interactions in asymmetric catalysis: Links between enzymes and small molecule catalysts
807 Citations2010Robert R. Knowles, Eric N. Jacobsen
Some recent efforts to elucidate the cooperative mechanisms responsible for stereoinduction in highly enantioselective reactions promoted by noncovalent catalysts are outlined.
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.
Angewandte Chemie International EditionCatalytic Asymmetric Hetero-Diels–Alder Reactions of Carbonyl Compounds and Imines
637 Citations2000Karl Anker Jørgensen
This review will focus on the most important developments, and discuss the synthetic and mechanistic aspects of enantioselective hetero-Diels-Alder reactions of carbonyl compounds catalyzed by chiral Lewis acids.
Angewandte Chemie International EditionThe Art and Science of Total Synthesis at the Dawn of the Twenty-First Century
590 Citations2000K. C. Nicolaou, Dionisios Vourloumis +2 more
This retrospective on total synthesis should serve to demonstrate how far the authors have come, yet show that the science of total synthesis is still in its infancy.
Chemical Society ReviewsChiral Brønsted acids in enantioselective carbonyl activations – activation modes and applications
538 Citations2011Magnus Rueping, Alexander Kuenkel +1 more
Different activation modes, key features of the catalysts and the applied substrates are presented and discussed with the goal to elucidate the origin of stereoselectivity in these Brønsted acid catalyzed transformations.
TetrahedronRecent synthetic developments in a powerful imino Diels–Alder reaction (Povarov reaction): application to the synthesis of N-polyheterocycles and related alkaloids
528 Citations2008Vladímir V. Kouznetsov
Angewandte Chemie International EditionRemovable Directing Groups in Organic Synthesis and Catalysis
523 Citations2011Géraldine Rousseau, Bernhard Breit
An overview of the state of the art in this area, including the stoichiometric and catalytic use of directing groups is given, as well as specific introduction of an appropriately designed removable reagent-directing group.
Topics in current chemistryChiral Brønsted Acids for Asymmetric Organocatalysis
472 Citations2009Daniela Kampen, Corinna M. Reisinger +1 more
Angewandte Chemie International EditionOxetanes as Versatile Elements in Drug Discovery and Synthesis
435 Citations2010Johannes A. Burkhard, Georg Wuitschik +3 more
This Minireview gives an overview of the recent advances made in the preparation and use of 3-substituted oxetanes and includes a discussion of the site-dependent modifications of various physicochemical and biochemical properties that result from the incorporation of the oxetane unit in molecular architectures.
Chemistry - A European JournalUnifying Metal and Brønsted Acid Catalysis—Concepts, Mechanisms, and Classifications
430 Citations2010Magnus Rueping, René M. Koenigs +1 more
The latest contributions in the field of combined chiral Brønsted acid and metal catalyzed reactions are presented, highlighting the advantages of these catalytic systems as well as describing the uncertainties regarding the molecular structure of the catalytically active species and the reaction mechanisms.
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.
Journal of Medicinal ChemistryOxetanes in Drug Discovery: Structural and Synthetic Insights
405 Citations2010Georg Wuitschik, Erick M. Carreira +6 more
A rich chemistry of oxetan-3-one and derived Michael acceptors provide venues for the preparation of a broad variety of novel oxetanes not previously documented, thus providing the foundation for their broad use in chemistry and drug discovery.
Journal of the American Chemical SocietyChiral Brønsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction
396 Citations2009Hua Liu, Guillaume Dagousset +3 more
The three-component Povarov reaction of aldehydes, anilines, and benzyl N-vinylcarbamate 4 in the presence of 0.1 equiv of chiral phosphoric acid afforded cis-2,4-disubstituted tetrahydroquinolines in good yields and excellent enantiomeric excesses.
Journal of the American Chemical SocietyChiral Brønsted Acid-Catalyzed Inverse Electron-Demand Aza Diels−Alder Reaction
390 Citations2006Takahiko Akiyama, Hisashi Morita +1 more
Inverse electron-demand aza Diels-Alder reaction of aldimine with enol ethers proceeded under the influence of a phosphoric acid diester, derived from (R)-BINOL, to give tetrahydroquinoline derivatives with excellent enantioselectivity.
Topics in current chemistryHetero Diels-Alder reactions in organic chemistry
368 Citations1997Lutz F. Tietze, Georg Kettschau
Angewandte ChemieNeue Entwicklungen in der asymmetrischen Mehrkomponenten‐Reaktion
363 Citations2005Diego J. Ramón, Miguel Yus
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.
Journal of the American Chemical SocietyKinetic Resolution of Homoaldols via Catalytic Asymmetric Transacetalization
331 Citations2010Ilija Čorić, Steffen Müller +1 more
A novel phosphoric acid, STRIP, based on a spirocyclic 1,1'-spirobiindane backbone was designed and identified as a superior catalyst for this transacetalization reaction, and both secondary and tertiary homoaldols gave equally excellent results.
Journal of the American Chemical SocietyChiral Phosphoric Acid-Catalyzed Enantioselective Three-Component Povarov Reaction Using Enecarbamates as Dienophiles: Highly Diastereo- and Enantioselective Synthesis of Substituted 4-Aminotetrahydroquinolines
274 Citations2011Guillaume Dagousset, Jieping Zhu +1 more
Angewandte ChemieNichtlineare Effekte bei asymmetrischen Synthesen und stereoselektiven Reaktionen
272 Citations1998Christian Girard, Henri B. Kagan
Journal of the American Chemical SocietyEnantioselective Halocyclization Using Reagents Tailored for Chiral Anion Phase-Transfer Catalysis
265 Citations2012Yiming Wang, Jeffrey C.S. Wu +3 more
A chiral anion phase-transfer system for enantioselective halogenation is described, and application of this system to o-anilidostyrenes afforded halogenated 4H-3,1-benzoxazines with excellent yield and en antioselectivity.
Angewandte Chemie International EditionDirect Catalytic Enantioselective Aza‐Diels–Alder Reactions
243 Citations2005Henrik Sundén, Ismail Ibrahem +2 more
Journal of the American Chemical SocietyMechanism of Amido-Thiourea Catalyzed Enantioselective Imine Hydrocyanation: Transition State Stabilization via Multiple Non-Covalent Interactions
237 Citations2009Stephan J. Zuend, Eric N. Jacobsen
Data are consistent with a mechanism involving catalyst-promoted proton transfer from hydrogen isocyanide to imine to generate diastereomeric iminium/cyanide ion pairs that are bound to catalyst through multiple noncovalent interactions; these ion pairs collapse to form the enantiomeric alpha-aminonitrile products.
European Journal of Organic ChemistryDiverse Strategies for the Synthesis of the Indoline Scaffold
218 Citations2010Dianyu Liu, Guowei Zhao +1 more
This microreview describes the recent advances in the synthesis of indoline derivatives, including Cu- and Pd-catalyzed reactions, metal-free approaches (radical reaction), as well as other types of reactions.
Angewandte Chemie International EditionAsymmetric Three‐Component Inverse Electron‐Demand Aza‐Diels–Alder Reaction: Efficient Synthesis of Ring‐Fused Tetrahydroquinolines
210 Citations2010Ming‐Sheng Xie, Xiaohong Chen +5 more
Organic LettersHighly Enantioselective Relay Catalysis in the Three-Component Reaction for Direct Construction of Structurally Complex Heterocycles
200 Citations2010Chao Wang, Zhi‐Yong Han +2 more
A highly enantioselective three-component cascade reaction provides a unique method to access structurally diverse julolidine derivatives in high optical purity.
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.
Journal of the American Chemical SocietyEnantioselective Intramolecular Openings of Oxetanes Catalyzed by (salen)Co(III) Complexes: Access to Enantioenriched Tetrahydrofurans
171 Citations2009Rebecca N. Loy, Eric N. Jacobsen
Angewandte ChemieKatalytische asymmetrische Hetero-Diels-Alder-Reaktionen von Carbonylverbindungen und Iminen
163 Citations2000Karl Anker Jørgensen
Angewandte ChemieEntfernbare dirigierende Gruppen in der organischen Synthese und Katalyse
160 Citations2011Géraldine Rousseau, Bernhard Breit
Angewandte ChemieDer Stand der Totalsynthese zu Beginn des 21. Jahrhunderts
138 Citations2000K. C. Nicolaou, Dionisios Vourloumis +2 more
Organic LettersCarboxylic Acid Catalyzed Three-Component Aza-Friedel−Crafts Reactions in Water for the Synthesis of 3-Substituted Indoles
133 Citations2006Seiji Shirakawa, Shu̅ Kobayashi
The carboxylic acid catalyzed three-component aza-Friedel-Crafts reactions of aldehydes, primary amines, and indoles in water have been developed and offers a novel efficient method for the synthesis of 3-substituted indoles.
Journal of the American Chemical SocietyThree-Component Ag-Catalyzed Enantioselective Vinylogous Mannich and Aza-Diels−Alder Reactions with Alkyl-Substituted Aldehydes
132 Citations2008Hiroki Mandai, Kyoko Mandai +2 more
Evidence is presented indicating that reactions with chiral nonracemic aldehydes are subject to catalyst control: both substrate enantiomers react to afford the desired product diastereomers in high stereoselectivity.
Angewandte ChemieOxetane als vielseitige Bausteine in der Wirkstoff‐Forschung und Synthese
114 Citations2010Johannes A. Burkhard, Georg Wuitschik +3 more
Organic LettersDirect Assembly of Aldehydes, Amino Esters, and Anilines into Chiral Imidazolidines via Brønsted Acid Catalyzed Asymmetric 1,3-Dipolar Cycloadditions
101 Citations2008Weijun Liu, Xiaohua Chen +1 more
A chiral Brønsted acid catalyzed 1,3-dipolar cycloaddition reaction directly assembles aldehydes, amino esters, and anilines into synthetically useful chiral imidazolidines with high levels of stereoselectivity.
Angewandte Chemie International EditionSynthesis of Eight‐Membered Lactones: Intermolecular [6+2] Cyclization of Amphoteric Molecules with Siloxy Alkynes
96 Citations2012Wanxiang Zhao, Zhaobin Wang +1 more
The design of a new type of amphoteric molecule for the synthesis of eight-membered ring lactones through [6+2] cyclization and identifies siloxy alkynes as excellent reaction partners for the (1,6)-amphoteric system to form eightmembered lactones.
Tetrahedron AsymmetryRoutes toward enantiopure 2-substituted indolines: an overview
91 Citations2009Saithalavi Anas, Henri B. Kagan
Journal of Medicinal ChemistryDevelopment of Tetrahydroisoquinoline-Based Hydroxamic Acid Derivatives: Potent Histone Deacetylase Inhibitors with Marked in Vitro and in Vivo Antitumor Activities
86 Citations2011Yingjie Zhang, Jinhong Feng +6 more
The results indicate that tetrahydroisoquinoline bearing a hydroxamic acid is an excellent template to develop novel HDACi as potential anticancer agents.
Chemistry - A European JournalChiral Phosphoric Acid‐Catalyzed Enantioselective Three‐Component Povarov Reaction Using Cyclic Enethioureas as Dienophiles: Stereocontrolled Access to Enantioenriched Hexahydropyrroloquinolines
83 Citations2012Guillaume Dagousset, Pascal Retailleau +2 more
Three become one: Phosphoric acid-catalyzed enantioselective three-component Povarov reactions of aldehydes, anilines, and endocyclic enethioureas have been developed and afforded hexahydropyrroloquinolines in high yields with excellent diastereo- and enantiOSElectivities.
Angewandte ChemieAsymmetric Three‐Component Inverse Electron‐Demand Aza‐Diels–Alder Reaction: Efficient Synthesis of Ring‐Fused Tetrahydroquinolines
81 Citations2010Ming‐Sheng Xie, Xiaohong Chen +5 more
Angewandte ChemieAsymmetrische Brønsted‐Säure‐katalysierte Synthese von Isoindolinen: Steigerung des Enantiomerenverhältnisses durch stereoablative kinetische Racematspaltung
77 Citations2008Dieter Enders, Arun A. Narine +2 more
Angewandte ChemieDirect Catalytic Enantioselective Aza‐Diels–Alder Reactions
75 Citations2005Henrik Sundén, Ismail Ibrahem +2 more
Bioorganic & Medicinal Chemistry Letters1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro
67 Citations2008Pi Cheng, Ning Huang +6 more
The results of the anti-HIV screening revealed that 6, 7-dihydroxytetrahydroisoquinolines possessed higher selective index than 6,7-dimethoxyl analogs due to the significantly decreased cytotoxicities.
Angewandte Chemie International EditionAsymmetric Amplification in Phosphoric Acid Catalyzed Reactions
52 Citations2010Nan Li, Xiaohua Chen +5 more
Angewandte ChemieSynthesis of Eight‐Membered Lactones: Intermolecular [6+2] Cyclization of Amphoteric Molecules with Siloxy Alkynes
40 Citations2012Wanxiang Zhao, Zhaobin Wang +1 more
European Journal of Organic ChemistryMulticomponent Reactions of Indole, Ethyl Glyoxylate and Anilines: From Friedel–Crafts to Aza‐Diels–Alder Reactions Catalysed by Scandium Triflate
25 Citations2009Giovanni Desimoni, Giuseppe Faita +3 more
Tetrahedron Letters(+) Melonine and NB-oxy melonine, a new indoline skeleton
25 Citations1983S. Baassou, H Mehri +2 more
Angewandte ChemieAsymmetric Amplification in Phosphoric Acid Catalyzed Reactions
18 Citations2010Nan Li, Xiaohua Chen +5 more
