Construction of Spirocyclic Oxindoles through Regio- and Stereoselective [3+2] or [3+2]/[4+2] Cascade Reaction of α,β-Unsaturated Imines with 3-Isothiocyanato Oxindole
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Title
Construction of Spirocyclic Oxindoles through Regio- and Stereoselective [3+2] or [3+2]/[4+2] Cascade Reaction of α,β-Unsaturated Imines with 3-Isothiocyanato Oxindole
Authors
Keywords
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Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 14, Pages 4733-4737
Publisher
Wiley
Online
2016-02-08
DOI
10.1002/chem.201600497
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Note: Only part of the references are listed.- Recent Advances of α-Isothiocyanato Compounds in the Catalytic Asymmetric Reaction
- (2015) Wen-Yong Han et al. ADVANCED SYNTHESIS & CATALYSIS
- Organocatalytic Asymmetric Addition of Naphthols and Electron-Rich Phenols to Isatin-Derived Ketimines: Highly Enantioselective Construction of Tetrasubstituted Stereocenters
- (2015) Marc Montesinos-Magraner et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Enantioselective [3+2] Cyclization of 3-Isothiocyanato Oxindoles with Trifluoromethylated 2-Butenedioic Acid Diesters
- (2015) Dan Du et al. ChemCatChem
- Facile access to a heterocyclic, sp3-rich chemical scaffold via a tandem condensation/intramolecular nitrone–alkene [3+2] cycloaddition strategy
- (2015) M. J. Rawling et al. CHEMICAL COMMUNICATIONS
- Manganese catalyzed C–H functionalization of indoles with alkynes to synthesize bis/trisubstituted indolylalkenes and carbazoles: the acid is the key to control selectivity
- (2015) Lijun Shi et al. CHEMICAL COMMUNICATIONS
- Gold(I)-Catalyzed Selective Heterocyclization of Propargylic Thioureas: Mechanistic Study of Competitive Gold-Activation Mode
- (2015) Yu Jiang et al. CHEMISTRY-A EUROPEAN JOURNAL
- Organocatalytic Enantioselective Direct Vinylogous Michael Addition of α,β-Unsaturated γ-Butyrolactam to β-Acyl Acrylates and 1,2-Diacylethylenes
- (2015) Yi-Ru Chen et al. JOURNAL OF ORGANIC CHEMISTRY
- Diastereoselective Synthesis of Dispirobarbiturates through Et3N-Catalyzed [3 + 2] Cycloaddition of Barbiturate-Based Olefins with 3-Isothiocyanato Oxindoles
- (2015) Hong-Wu Zhao et al. JOURNAL OF ORGANIC CHEMISTRY
- Diastereo- and Enantioselective Construction of 3,3′-Pyrrolidinyldispirooxindole Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions
- (2015) Wei Dai et al. JOURNAL OF ORGANIC CHEMISTRY
- From meso-Lactide to Isotactic Polylactide: Epimerization by B/N Lewis Pairs and Kinetic Resolution by Organic Catalysts
- (2015) Jian-Bo Zhu et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Organocatalytic regioselective asymmetric Michael addition of azlactones to o-hydroxy chalcone derivatives
- (2015) Shao-Yun Zhang et al. ORGANIC & BIOMOLECULAR CHEMISTRY
- Catalytic Asymmetric [3 + 2] Cyclization Reactions of 3-Isothiocyanato Oxindoles and Alkynyl Ketones Via an in Situ Generated Magnesium Catalyst
- (2015) Linqing Wang et al. ORGANIC LETTERS
- Zn-Catalyzed Diastereo- and Enantioselective Cascade Reaction of 3-Isothiocyanato Oxindoles and 3-Nitroindoles: Stereocontrolled Syntheses of Polycyclic Spirooxindoles
- (2015) Jian-Qiang Zhao et al. ORGANIC LETTERS
- Asymmetric Michael/Cyclization Cascade Reaction of 3-Isothiocyanato Oxindoles and 3-Nitroindoles with Amino-Thiocarbamate Catalysts: Enantioselective Synthesis of Polycyclic Spirooxindoles
- (2015) Jian-Qiang Zhao et al. ORGANIC LETTERS
- Catalytic Aldol–Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates
- (2015) Satavisha Kayal et al. ORGANIC LETTERS
- Enantioselective Synthesis of Functionalized Polycarbocycles via a Three-Component Organocascade Quadruple Reaction
- (2015) Yun-Pu Chang et al. ORGANIC LETTERS
- Catalytic Enantioselective Ring-Opening and Ring-Closing Reactions of 3-Isothiocyanato Oxindoles and N-(2-Picolinoyl)aziridines
- (2015) Linqing Wang et al. ORGANIC LETTERS
- Quinine-catalyzed asymmetric domino Mannich-cyclization reactions of 3-isothiocyanato oxindoles with imines for the synthesis of spirocyclic oxindoles
- (2015) Mei Bai et al. TETRAHEDRON
- Unprecedented Hydrophobic Amplification in Noncovalent Organocatalysis “on Water”: Hydrophobic Chiral Squaramide Catalyzed Michael Addition of Malonates to Nitroalkenes
- (2015) Han Yong Bae et al. ACS Catalysis
- Cobalt(II)-Catalyzed Oxidative C–H Alkenylations: Regio- and Site-Selective Access to Isoindolin-1-one
- (2015) Wenbo Ma et al. ACS Catalysis
- Organocatalytic Enantioselective Sulfur-Michael Addition of Thioacetic Acid to Arylmethylidenemalonates
- (2014) Renchao Wang et al. ADVANCED SYNTHESIS & CATALYSIS
- Catalytic Enantioselective Carboannulation with Allylsilanes
- (2014) Nicolas R. Ball-Jones et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Engineering of P450pyr Hydroxylase for the Highly Regio- and Enantioselective Subterminal Hydroxylation of Alkanes
- (2014) Yi Yang et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Amide Synthesis by Nucleophilic Attack of Vinyl Azides
- (2014) Feng-Lian Zhang et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- A Mannich/cyclization cascade process for the asymmetric synthesis of spirocyclic thioimidazolidineoxindoles
- (2014) Hao Cai et al. CHEMICAL COMMUNICATIONS
- Enantioselective Cascade Michael Addition/Cyclization Reactions of 3-Nitro-2H-Chromenes with 3-Isothiocyanato Oxindoles: Efficient Synthesis of Functionalized Polycyclic Spirooxindoles
- (2014) Fen Tan et al. CHEMISTRY-A EUROPEAN JOURNAL
- Novel Organocatalytic Activation of Unmodified Morita-Baylis-Hillman Alcohols for the Synthesis of Bicyclic α-Alkylidene-Ketones
- (2014) Julian Stiller et al. CHEMISTRY-A EUROPEAN JOURNAL
- Catalytic Enantioselective Amide Allylation of Isatins and Its Application in the Synthesis of 2-Oxindole Derivatives Spiro-Fused to the α-Methylene-γ-Butyrolactone Functionality
- (2014) Masaki Takahashi et al. CHEMISTRY-A EUROPEAN JOURNAL
- Organocatalyzed Asymmetric 1,4-Addition of Azlactones to α,β-Unsaturated Trichloromethyl Ketones: Synthesis of α,α-Disubstituted α-Amino Acid Derivatives
- (2014) Jinlong Zhang et al. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- Catalytic Asymmetric Michael Addition/Cyclization Cascade Reaction of 3-Isothiocyanatooxindoles with Nitro Olefins
- (2014) Satavisha Kayal et al. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- Tandem Michael Addition–Ring Transformation Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with Olefinic Azlactones: Direct Access to Structurally Diverse Spirocyclic Oxindoles
- (2014) Bao-Dong Cui et al. JOURNAL OF ORGANIC CHEMISTRY
- An Organocatalytic Michael–Michael Cascade for the Enantioselective Construction of Spirocyclopentane Bioxindoles: Control of Four Contiguous Stereocenters
- (2014) Wangsheng Sun et al. ORGANIC LETTERS
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- (2014) Nandini Sharma et al. ORGANIC LETTERS
- Quinine-catalyzed asymmetric domino Michael-cyclization reaction for the synthesis of spirocyclic oxindoles bearing two spiro quaternary centers and three consecutive stereocenters
- (2014) Bao-Dong Cui et al. TETRAHEDRON
- Organocatalytic domino Michael/cyclization reaction: efficient synthesis of multi-functionalized tetracyclic spirooxindoles with multiple stereocenters
- (2014) Zu-Kang Fu et al. RSC Advances
- Enantioselective Construction of Spirooxindole Derivatives: Asymmetric [3+2] Cyclization of Isothiocyanatooxindoles with Allenic Esters or 2-Butynedioic Acid Diesters
- (2013) Dan Du et al. ADVANCED SYNTHESIS & CATALYSIS
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- (2013) Xu Tian et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- An asymmetric approach toward chiral multicyclic spirooxindoles from isothiocyanato oxindoles and unsaturated pyrazolones by a chiral tertiary amine thiourea catalyst
- (2013) Qiao Chen et al. CHEMICAL COMMUNICATIONS
- Asymmetric synthesis of 3-spirocyclopropyl-2-oxindoles via intramolecular trapping of chiral aza-ortho-xylylene
- (2013) Xiaowei Dou et al. CHEMICAL COMMUNICATIONS
- Counterion effects in the catalytic stereoselective synthesis of 2,3′-pyrrolidinyl spirooxindoles
- (2013) Jacob P. MacDonald et al. CHEMICAL COMMUNICATIONS
- 3-Isothiocyanato Oxindoles Serving as Powerful and Versatile Precursors to Structurally Diverse Dispirocyclic Thiopyrrolidineoxindoles through a Cascade Michael/Cyclization Process with Amino-Thiocarbamate Catalysts
- (2013) Wen-Yong Han et al. CHEMISTRY-A EUROPEAN JOURNAL
- Enantioselective Synthesis of Spirooxindoles: Asymmetric [3+2] Cycloaddition of (3-Isothiocyanato)oxindoles with Azodicarboxylates
- (2013) Yu Jiang et al. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- Enantioselective Synthesis of Spirooxindoles via Direct Catalytic Asymmetric Aldol-Type Reaction of Isothiocyanato Oxindoles
- (2013) Shigeki Matsunaga et al. HETEROCYCLES
- A Coupling of Benzamides and Donor/Acceptor Diazo Compounds To Form γ-Lactams via Rh(III)-Catalyzed C–H Activation
- (2013) Todd K. Hyster et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Highly Efficient and Stereocontrolled Construction of 3,3′-Pyrrolidonyl Spirooxindoles via Organocatalytic Domino Michael/Cyclization Reaction
- (2013) Xiong-Li Liu et al. ORGANIC LETTERS
- Base-Catalyzed Diastereoselective [3 + 3] Annulation of 3-Isothiocyanatooxindoles and Azomethine Imines
- (2013) Gongming Zhu et al. ORGANIC LETTERS
- Highly efficient synthesis of spiro[oxazolidine-2-thione-oxindoles] with 3-isothiocyanato oxindoles and aldehydes via an organocatalytic cascade aldol-cyclization reaction
- (2013) Wen-Bing Chen et al. TETRAHEDRON
- Highly efficient and diastereoselective construction of bispirooxindoles through a cascade Michael-cyclization reaction
- (2013) Song Wu et al. TETRAHEDRON
- cis-Enals in N-heterocyclic carbene-catalyzed reactions: distinct stereoselectivity and reactivity
- (2013) Xingkuan Chen et al. Chemical Science
- A Concise Assembly of Electron-Deficient 2,4-Dienes and 2,4-Dienals: Regio- and Stereoselectiveexo-Diels-Alder and Redox Reactions through Sequential Amine and Carbene Catalysis
- (2012) Chao Ma et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Catalytic Asymmetric Synthesis of Spirooxindoles by a Mannich-Type Reaction of Isothiocyanato Oxindoles
- (2012) Shota Kato et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Catalytic Selective Synthesis
- (2012) Jessada Mahatthananchai et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Diastereodivergent Synthesis of 3-Spirocyclopropyl-2-oxindoles through Direct Enantioselective Cyclopropanation of Oxindoles
- (2012) Xiaowei Dou et al. CHEMISTRY-A EUROPEAN JOURNAL
- Highly Efficient Enantioselective Construction of Bispirooxindoles Containing Three Stereocenters through an Organocatalytic Cascade Michael-Cyclization Reaction
- (2012) Hao Wu et al. CHEMISTRY-A EUROPEAN JOURNAL
- Catalytic Asymmetric Michael Addition/Cyclization of Isothiocyanato Oxindoles: Highly Efficient and Versatile Approach for the Synthesis of 3,2′-Pyrrolidinyl Mono- and Bi-spirooxindole Frameworks
- (2012) Yi-Ming Cao et al. CHEMISTRY-A EUROPEAN JOURNAL
- Asymmetric Synthesis of Enaminophosphines via Palladacycle-Catalyzed Addition of Ph2PH to α,β-Unsaturated Imines
- (2012) Yinhua Huang et al. JOURNAL OF ORGANIC CHEMISTRY
- Strategies for the enantioselective synthesis of spirooxindoles
- (2012) Nicolas R. Ball-Jones et al. ORGANIC & BIOMOLECULAR CHEMISTRY
- Hydrogen-Bond-Mediated Cascade Reaction Involving Chalcones: Facile Synthesis of Enantioenriched Trisubstituted Tetrahydrothiophenes
- (2012) Jun-Bing Ling et al. ORGANIC LETTERS
- Highly Efficient and Stereoselective Construction of Dispiro-[oxazolidine-2-thione]bisoxindoles and Dispiro[imidazolidine-2-thione]bisoxindoles
- (2012) Yan-Yan Han et al. ORGANIC LETTERS
- Enantioselective Intramolecular Formal [2 + 4] Annulation of Acrylates and α,β-Unsaturated Imines Catalyzed by Amino Acid Derived Phosphines
- (2012) Zhichao Jin et al. ORGANIC LETTERS
- Highly enantioselective [4 + 2] annulations catalyzed by amino acid-based phosphines: Synthesis of functionalized cyclohexenes and 3-spirocyclohexene-2-oxindoles
- (2012) Fangrui Zhong et al. Chemical Science
- Brønsted-Acid-Catalyzed Asymmetric Multicomponent Reactions for the Facile Synthesis of Highly Enantioenriched Structurally Diverse Nitrogenous Heterocycles
- (2011) Jie Yu et al. ACCOUNTS OF CHEMICAL RESEARCH
- Highly Enantioselective [3+2] Annulation of Morita-Baylis-Hillman Adducts Mediated by L-Threonine-Derived Phosphines: Synthesis of 3-Spirocyclopentene-2-oxindoles having Two Contiguous Quaternary Centers
- (2011) Fangrui Zhong et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Dioxindole in Asymmetric Catalytic Synthesis: Routes to Enantioenriched 3-Substituted 3-Hydroxyoxindoles and the Preparation of Maremycin A
- (2011) Giulia Bergonzini et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis
- (2011) José Alemán et al. CHEMISTRY-A EUROPEAN JOURNAL
- Core-Structure-Motivated Design of a Phosphine-Catalyzed [3 + 2] Cycloaddition Reaction: Enantioselective Syntheses of Spirocyclopenteneoxindoles
- (2011) Bin Tan et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Organocatalytic Direct Asymmetric Aldol Reactions of 3-Isothiocyanato Oxindoles to Ketones: Stereocontrolled Synthesis of Spirooxindoles Bearing Highly Congested Contiguous Tetrasubstituted Stereocenters
- (2011) Wen-Bing Chen et al. ORGANIC LETTERS
- Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C-3 Position
- (2010) Feng Zhou et al. ADVANCED SYNTHESIS & CATALYSIS
- A Unique Approach to the Concise Synthesis of Highly Optically Active Spirooxazolines and the Discovery of a More Potent Oxindole-Type Phytoalexin Analogue
- (2010) Xianxing Jiang et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Efficient stereo- and regioselective hydroxylation of alkanes catalysed by a bulky polyoxometalate
- (2010) Keigo Kamata et al. Nature Chemistry
- Spiroindolones, a Potent Compound Class for the Treatment of Malaria
- (2010) M. Rottmann et al. SCIENCE
- An enantioselective organocatalyzed aza-MBH domino process: application to the facile synthesis of tetrahydropyridines
- (2010) Shinobu Takizawa et al. TETRAHEDRON LETTERS
- Highly enantioselective intramolecular aza-spiroannulation onto indoles using chiral rhodium catalysis: asymmetric entry to the spiro-β-lactam core of chartellines
- (2009) Shigeki Sato et al. CHEMICAL COMMUNICATIONS
- Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity
- (2009) Xiao-Hua Chen et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Organocatalytic Asymmetric Inverse-Electron-Demand Aza-Diels-Alder Reaction ofN-Sulfonyl-1-aza-1,3-butadienes and Aldehydes
- (2008) Bo Han et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Synthesis of novel spiropyrrolizidines as potent antimicrobial agents for human and plant pathogens
- (2008) Govindasami Periyasami et al. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
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- (2008) Xiangtai Meng et al. CHEMISTRY-A EUROPEAN JOURNAL
- Direct Catalytic Asymmetric Synthesis of Cyclic Aminals from Aldehydes
- (2008) Xu Cheng et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- A novel and facile stereocontrolled synthetic method for polyhydro-quinolines and pyridopyridazines via a diene-transmissive Diels–Alder reaction involving inverse electron-demand hetero Diels–Alder cycloaddition of cross-conjugated azatrienes
- (2008) Satoru Kobayashi et al. TETRAHEDRON
- A diene-transmissive Diels–Alder reaction involving inverse electron-demand hetero-Diels–Alder cycloaddition of cross-conjugated azatrienes
- (2008) Satoru Kobayashi et al. TETRAHEDRON LETTERS
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