Phosphine-mediated Highly Enantioselective Spirocyclization with Ketimines as Substrates

Diastereo- and Enantioselective Synthesis of Chiral Pyrrolidine-Fused SpirooxindolesviaOrganocatalytic [3+2] 1,3-Dipolar Cycloaddition of Azomethine Ylides with Maleimides

(2015) Hong-Wu Zhao et al.   ADVANCED SYNTHESIS & CATALYSIS

Phosphahelicenes in Asymmetric Organocatalysis: [3+2] Cyclizations of γ-Substituted Allenes and Electron-Poor Olefins

(2015) Maxime Gicquel et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

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 synthesis of 3-fluoro-3-allyl-oxindoles via phosphine-catalyzed asymmetric γ-addition of 3-fluoro-oxindoles to 2,3-butadienoates

(2015) Tianli Wang et al.   CHEMICAL COMMUNICATIONS

The asymmetric synthesis of CF3-containing spiro[pyrrolidin-3,2′-oxindole] through the organocatalytic 1,3-dipolar cycloaddition reaction

(2015) Mingxia Ma et al.   CHEMICAL COMMUNICATIONS

Catalytic Asymmetric Construction of Vicinal Tetrasubstituted Stereocenters by the Mannich Reaction of Linear α-Substituted Monothiomalonates with Isatin N-Boc Ketimines

(2015) Teng Liu 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

Use of a New Spirophosphine To Achieve Catalytic Enantioselective [4 + 1] Annulations of Amines with Allenes To Generate Dihydropyrroles

(2015) Søren Kramer et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Phosphine-Catalyzed Enantioselective Intramolecular [3+2] Annulations To Generate Fused Ring Systems

(2015) Sarah Yunmi Lee et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Phosphine-Catalyzed Doubly Stereoconvergent γ-Additions of Racemic Heterocycles to Racemic Allenoates: The Catalytic Enantioselective Synthesis of Protected α,α-Disubstituted α-Amino Acid Derivatives

(2015) Marcin Kalek et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

(2015) Tianli Wang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides

(2015) Abdulrahman Almansour et al.   MOLECULES

A Facile Ionic Liquid Promoted Synthesis, Cholinesterase Inhibitory Activity and Molecular Modeling Study of Novel Highly Functionalized Spiropyrrolidines

(2015) Abdulrahman Almansour et al.   MOLECULES

Maleimide as an efficient nucleophilic partner in the aza-Morita–Baylis–Hillman reaction: synthesis of chiral 3-substituted-3-aminooxindoles

(2015) Akshay Kumar et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Morita–Baylis–Hillman adduct derivatives (MBHADs): versatile reactivity in Lewis base-promoted annulation

(2015) Peizhong Xie et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

An Organocatalytic Asymmetric Friedel–Crafts Addition/Fluorination Sequence: Construction of Oxindole–Pyrazolone Conjugates Bearing Vicinal Tetrasubstituted Stereocenters

(2015) Xiaoze Bao et al.   ORGANIC LETTERS

First stereospecific total synthesis of (−)-affinisine oxindole as well as facile entry into the C(7)-diastereomeric chitosenine stereochemistry

(2015) German O. Fonseca et al.   TETRAHEDRON LETTERS

Highly enantioselective construction of tertiary thioethers and alcohols via phosphine-catalyzed asymmetric γ-addition reactions of 5H-thiazol-4-ones and 5H-oxazol-4-ones: scope and mechanistic understandings

(2015) Tianli Wang et al.   Chemical Science

PyBidine-Cu(OTf)2-Catalyzed Asymmetric [3+2] Cycloaddition with Imino Esters: Harmony of Cu-Lewis Acid and Imidazolidine-NH Hydrogen Bonding in Concerto Catalysis

(2014) Takayoshi Arai et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Phosphine-Catalyzed Enantioselective γ-Addition of 3-Substituted Oxindoles to 2,3-Butadienoates and 2-Butynoates: Use of Prochiral Nucleophiles

(2014) Tianli Wang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Asymmetric Synthesis of Spiropyrazolones through Phosphine-Catalyzed [4+1] Annulation

(2014) Xiaoyu Han et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Enantioselective Construction of Vicinal Tetrasubstituted Stereocenters by the Mannich Reaction of Silyl Ketene Imines with Isatin-Derived Ketimines

(2014) Jiannan Zhao et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Chiral phosphines in nucleophilic organocatalysis

(2014) Yumei Xiao et al.   Beilstein Journal of Organic Chemistry

Highly enantioselective aza-Henry reaction with isatin N-Boc ketimines

(2014) Melireth Holmquist et al.   CHEMICAL COMMUNICATIONS

Phosphine catalysis of allenes with electrophiles

(2014) Zhiming Wang et al.   CHEMICAL SOCIETY REVIEWS

Asymmetric Organocatalyzed Michael Addition of Nitromethane to a 2-Oxoindoline-3-ylidene Acetaldehyde and the Three One-Pot Sequential Synthesis of (−)-Horsfiline and (−)-Coerulescine

(2014) Takasuke Mukaiyama et al.   CHEMISTRY-A EUROPEAN JOURNAL

A Phosphine-Catalyzed Novel Asymmetric [3+2] Cycloaddition of C,N-Cyclic Azomethine Imines with δ-Substituted Allenoates

(2014) De Wang et al.   CHEMISTRY-A EUROPEAN JOURNAL

Applications of Chiral Phosphine-Based Organocatalysts in Catalytic Asymmetric Reactions

(2014) Yin Wei et al.   Chemistry-An Asian Journal

Organocatalyzed Enantioselective Mannich Reaction of Pyrazoleamides with Isatin-Derived Ketimines

(2014) Tian-Ze Li et al.   JOURNAL OF ORGANIC CHEMISTRY

Diastereo- and Enantioselective Addition of Anilide-Functionalized Allenoates to N-Acylimines Catalyzed by a Pyridylalanine-Based Peptide

(2014) Curren T. Mbofana et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Highly Enantioselective, Intermolecular Hydroamination of Allenyl Esters Catalyzed by Bifunctional Phosphinothioureas

(2014) Yuan-Qing Fang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Hydroxyproline-Derived Pseudoenantiomeric [2.2.1] Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (−)-Pyrrolines

(2014) Christopher E. Henry et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Highly Enantioselective Synthesis of 3,4-Dihydropyrans through a Phosphine-Catalyzed [4+2] Annulation of Allenones and β,γ-Unsaturated α-Keto Esters

(2014) Weijun Yao et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The ever-expanding role of asymmetric covalent organocatalysis in scalable, natural product synthesis

(2014) Mikail E. Abbasov et al.   NATURAL PRODUCT REPORTS

Enantioselective aza-Morita–Baylis–Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles

(2014) Xuan Zhao et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Lewis Acid Catalyzed Unprecedented [3 + 2] Cycloaddition Yields 3,3′-Pyrrolidinyldispirooxindoles Containing Four Contiguous Chiral Stereocenters with Two Contiguous Quaternary Spirostereocenters

(2014) Koorathota Suman et al.   ORGANIC LETTERS

Bis(imidazolidine)pyridine-NiCl2 Catalyst for Nitro-Mannich Reaction of Isatin-Derived N-Boc Ketimines: Asymmetric Synthesis of Chiral 3-Substituted 3-Amino-2-oxindoles

(2014) Takayoshi Arai et al.   ORGANIC LETTERS

Phosphine Organocatalysis for the Synthesis of Spirocyclic Compounds

(2014) Arnaud Voituriez et al.   SYNLETT

Organocatalytic enantioselective aza-Henry reaction of ketimines derived from isatins: access to optically active 3-amino-2-oxindoles

(2014) Akshay Kumar et al.   RSC Advances

An Organocatalytic Addition of Nitromethane to Activated Ketimines

(2014) Yu-Hui Wang et al.   Asian Journal of Organic Chemistry

Enantioselective Organocatalyzed Formal [4+2] Cycloaddition of Ketimines with Allenoates: Easy Access to a Tetrahydropyridine Framework with a Chiral Tetrasubstituted Stereogenic Carbon Center

(2014) Shinobu Takizawa et al.   Asian Journal of Organic Chemistry

Efficient construction of highly functionalized spiro[γ-butyrolactone-pyrrolidin-3,3′-oxindole] tricyclic skeletons via an organocatalytic 1,3-dipolar cycloaddition

(2013) Long Wang et al.   CHEMICAL COMMUNICATIONS

Organocatalytic asymmetric multicomponent cascade reaction via 1,3-proton shift and [3+2] cycloaddition: an efficient strategy for the synthesis of oxindole derivatives

(2013) Li Tian et al.   CHEMICAL COMMUNICATIONS

P-chirogenic organocatalysts: application to the aza-Morita–Baylis–Hillman (aza-MBH) reaction of ketimines

(2013) Shinobu Takizawa et al.   CHEMICAL COMMUNICATIONS

Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs

(2013) Yi Chiao Fan et al.   CHEMICAL COMMUNICATIONS

Enantioselective Squaramide-Catalysed Domino Mannich-Cyclization Reaction of Isatin Imines

(2013) Xi-Bo Wang et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Phosphine-Catalyzed [3 + 2] Cycloaddition of Sulfamate-Derived Cyclic Imines with Allenoate: Synthesis of Sulfamate-Fused Dihydropyrroles

(2013) Hao Yu et al.   JOURNAL OF ORGANIC CHEMISTRY

Asymmetric catalytic aza-Morita–Baylis–Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers

(2013) Fang-Le Hu et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Highly Efficient and Stereocontrolled Construction of 3,3′-Pyrrolidonyl Spirooxindoles via Organocatalytic Domino Michael/Cyclization Reaction

(2013) Xiong-Li Liu et al.   ORGANIC LETTERS

Bisphosphine-Triggered One-Pot Sequential [3 + 2]/[3 + 2] Annulation of Allenoates with Cyclic Ketimines

(2013) Li-Jun Yang et al.   ORGANIC LETTERS

An efficient, one-pot, three-component procedure for the synthesis of chiral spirooxindolopyrrolizidines via catalytic highly enantioselective 1,3-dipolar cycloaddition

(2013) Farbod Salahi et al.   TETRAHEDRON LETTERS

Chiral Phosphine Catalyzed Asymmetric Michael Addition of Oxindoles

(2012) Fangrui Zhong et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Organocatalytic stereocontrolled synthesis of 3,3′-pyrrolidinyl spirooxindoles by [3+2] annulation of isocyanoesters with methyleneindolinones

(2012) Liang-Liang Wang et al.   CHEMICAL COMMUNICATIONS

The highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines catalyzed by chiral phosphoric acids

(2012) Jingchao Feng et al.   CHEMICAL COMMUNICATIONS

Organocatalytic asymmetric cyanation of isatin derived N-Boc ketoimines

(2012) Yun-Lin Liu et al.   CHEMICAL COMMUNICATIONS

Enantioselective Synthesis of AG-041R by using N-Heteroarenesulfonyl Cinchona Alkaloid Amides as Organocatalysts

(2012) Noriyuki Hara 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

Highly Enantioselective Regiodivergent Allylic Alkylations of MBH Carbonates with Phthalides

(2012) Fangrui Zhong et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective synthesis of 3,3′-dihydropyrryl-spirooxindoles via an organocatalytic three-component reaction

(2012) Wen-Tao Wei et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Asymmetric Construction of Functionalized Bicyclic Imides via [3 + 2] Annulation of MBH Carbonates Catalyzed by Dipeptide-Based Phosphines

(2012) Fangrui Zhong et al.   ORGANIC LETTERS

Highly Enantioselective Addition of Enals to Isatin-Derived Ketimines Catalyzed by N-Heterocyclic Carbenes: Synthesis of Spirocyclic γ-Lactams

(2012) Hui Lv et al.   ORGANIC LETTERS

Synthesis of N-Alkoxycarbonyl Ketimines Derived from Isatins and Their Application in Enantioselective Synthesis of 3-Aminooxindoles

(2012) Wenjin Yan 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

Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3 + 2] annulation

(2012) Ian P. Andrews et al.   Chemical Science

Enantioselective Michael/Cyclization Reaction Sequence: Scaffold-Inspired Synthesis of Spirooxindoles with Multiple Stereocenters

(2011) Yiming Cao et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Versatile Enantioselective [3+2] Cyclization between Imines and Allenoates Catalyzed by Dipeptide-Based Phosphines

(2011) Xiaoyu Han et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

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

Development of asymmetric phosphine-promoted annulations of allenes with electron-deficient olefins and imines

(2011) Qian-Yi Zhao et al.   CHEMICAL COMMUNICATIONS

Asymmetric [3+2] annulation of allenes with maleimides catalyzed by dipeptide-derived phosphines: facile creation of functionalized bicyclic cyclopentenes containing two tertiary stereogenic centers

(2011) Qianyi Zhao et al.   CHEMICAL COMMUNICATIONS

Catalytic [2+2] and [3+2] cycloaddition reactions of allenoates with cyclic ketimines

(2011) Xiang-Yu Chen et al.   CHEMICAL COMMUNICATIONS

Core Structure-Based Design of Organocatalytic [3+2]-Cycloaddition Reactions: Highly Efficient and Stereocontrolled Syntheses of 3,3′-Pyrrolidonyl Spirooxindoles

(2011) Bin Tan et al.   CHEMISTRY-A EUROPEAN JOURNAL

Bifunctional N-Acyl-Aminophosphine-Catalyzed Asymmetric [4+2] Cycloadditions of Allenoates and Imines

(2011) Hua Xiao et al.   CHEMISTRY-A EUROPEAN JOURNAL

Aplexone targets the HMG-CoA reductase pathway and differentially regulates arteriovenous angiogenesis

(2011) J. Choi et al.   DEVELOPMENT

Application of a New Chiral Phosphepine to the Catalytic Asymmetric Synthesis of Highly Functionalized Cyclopentenes That Bear an Array of Heteroatom-Substituted Quaternary Stereocenters

(2011) Yuji Fujiwara et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective [3 + 2] Cycloaddition of Allenes to Acrylates Catalyzed by Dipeptide-Derived Phosphines: Facile Creation of Functionalized Cyclopentenes Containing Quaternary Stereogenic Centers

(2011) Xiaoyu Han et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective Morita–Baylis–Hillman reaction promoted by l-threonine-derived phosphine–thiourea catalysts

(2011) Xiaoyu Han et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

l-Threonine-Derived Novel Bifunctional Phosphine−Sulfonamide Catalyst-Promoted Enantioselective Aza-Morita−Baylis−Hillman Reaction

(2011) Fangrui Zhong et al.   ORGANIC LETTERS

Diversity through phosphine catalysis identifies octahydro-1,6-naphthyridin-4-ones as activators of endothelium-driven immunity

(2011) D. Cruz et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Enantioselective synthesis of the spirotryprostatin A scaffold

(2011) Andrey P. Antonchick et al.   TETRAHEDRON

Phosphine-catalyzed one-pot isomerization of 3-alkynoates and [2 + 3]-cycloaddition with imines: formal synthesis of Securinega alkaloid (±)-allosecurinine

(2011) Magesh Sampath et al.   Chemical Science

Enantioselective carbon–sulfur bond formation: γ additions of aryl thiols to allenoates catalyzed by a chiral phosphepine

(2011) Yuji Fujiwara et al.   Chemical Science

Identification of a novel Vpr-binding compound that inhibits HIV-1 multiplication in macrophages by chemical array

(2010) Kyoji Hagiwara et al.   BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS

Diversity Through a Branched Reaction Pathway: Generation of Multicyclic Scaffolds and Identification of Antimigratory Agents

(2010) Zhiming Wang et al.   CHEMISTRY-A EUROPEAN JOURNAL

Phosphine-Catalyzed Formation of Carbon−Sulfur Bonds: Catalytic Asymmetric Synthesis of γ-Thioesters

(2010) Jianwei Sun et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products

(2010) Andrey P. Antonchick et al.   Nature Chemistry

A reversible fluorescent Hg2+ chemosensor based on a receptor composed of a thiol atom and an alkene moiety for living cell fluorescence imaging

(2010) Weiying Lin et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Catalytic asymmetric 1,3-dipolar cycloaddition of N-unprotected 2-oxoindolin-3-ylidene derivatives and azomethine ylides for the construction of spirooxindole-pyrrolidines

(2010) Tang-Lin Liu et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Pyridylalanine (Pal)-Peptide Catalyzed Enantioselective Allenoate Additions toN-Acyl Imines Proceed via an Atypical “aza-Morita−Baylis−Hillman” Mechanism

(2010) Lindsey B. Saunders et al.   ORGANIC LETTERS

Phosphine-catalyzed asymmetric additions of malonate esters to  -substituted allenoates and allenamides

(2010) R. Sinisi et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Enantioselective catalysis and complexity generation from allenoates

(2009) Bryan J. Cowen et al.   CHEMICAL SOCIETY REVIEWS

Pyridylalanine (Pal)-Peptide Catalyzed Enantioselective Allenoate Additions toN-Acyl Imines

(2009) Bryan J. Cowen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

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

In vivo antitumor effect of a novel inhibitor of protein geranylgeranyltransferase-I

(2009) J. Lu et al.   MOLECULAR CANCER THERAPEUTICS

Enantioselective Phosphine Organocatalysis

(2009) Angela Marinetti et al.   SYNLETT

Phosphine-triggered synthesis of functionalized cyclic compounds

(2008) Long-Wu Ye et al.   CHEMICAL SOCIETY REVIEWS

Inhibitors of Protein Geranylgeranyltransferase I and Rab Geranylgeranyltransferase Identified from a Library of Allenoate-derived Compounds

(2008) Masaru Watanabe et al.   JOURNAL OF BIOLOGICAL CHEMISTRY

Discovery of Antimycobacterial Spiro-piperidin-4-ones: An Atom Economic, Stereoselective Synthesis, and Biological Intervention

(2008) Raju Ranjith Kumar et al.   JOURNAL OF MEDICINAL CHEMISTRY

Cooperative, Highly Enantioselective Phosphinothiourea Catalysis of Imine−Allene [3 + 2] Cycloadditions

(2008) Yuan-Qing Fang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY