Enantioselective 1,6-Michael addition of anthrone to 3-methyl-4-nitro-5-alkenyl-isoxazoles catalyzed by bifunctional thiourea-tertiary amines
TetrahedronPublished 19 April 2011
Hongwei Sun, Yu‐Hua Liao, Zhijun Wu, Haoyu Wang, Xiaomei Zhang, Wei‐Cheng Yuan
Citations55
SJR quartileQ3
SJR score0.43
SNIP0.60
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
A simple and efficient method for the enantioselective 1,6-Michael addition reaction of anthrone to a series of 3-methyl-4-nitro-5-alkenyl-isoxazoles with a bifunctional thiourea-tertiary amine as catalyst is described.
Abstract
A simple and efficient method for the enantioselective 1,6-Michael addition reaction of anthrone to a series of 3-methyl-4-nitro-5-alkenyl-isoxazoles with a bifunctional thiourea-tertiary amine as catalyst is described. This transformation proceeds smoothly with 10 mol % catalyst and provides a series of Michael adducts bearing 3-methyl-4-nitro-isoxazole and anthrone units with good to high enantioselectivities (up to 96% ee) and in very high yields (up to 99%).
Keywords
Chemistry
Angewandte Chemie International EditionIn the Golden Age of Organocatalysis
2,574 Citations2004Peter I. Dalko, Lionel Moisan
The diverse examples show that in recent years organocatalysis has developed within organic chemistry into its own subdiscipline, whose "Golden Age" has already dawned.
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.
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.
Accounts of Chemical ResearchOn Inventing Reactions for Atom Economy
1,302 Citations2002Barry M. Trost
Using mechanistic reasoning, over 20 new processes of varying complexity have been designed and implemented that involved C-C bond-forming reactions and the prospect for such developments is probed in the context of ruthenium-catalyzed reactions.
Angewandte Chemie International EditionDiphenylprolinol Silyl Ethers as Efficient Organocatalysts for the Asymmetric Michael Reaction of Aldehydes and Nitroalkenes
1,257 Citations2005Yujiro Hayashi, Hiroaki Gotoh +2 more
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.
European Journal of Organic ChemistryRecent Advances in Asymmetric Organocatalytic 1,4‐Conjugate Additions
1,146 Citations2007Svetlana B. Tsogoeva
Journal of the American Chemical SocietyEnantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea
1,044 Citations2004Tomotaka Okino, Yasutaka Hoashi +3 more
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.
ChemInformEnantio‐ and Diastereoselective Michael Reaction of 1,3‐Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea.
863 Citations2005Tomotaka Okino, Yasutaka Hoashi +3 more
Tetrahedron AsymmetryOrganocatalytic asymmetric conjugate additions
857 Citations2007Diana Almaşi, Diego A. Alonso +1 more
An overview of the most important developments and concepts of this flourishing area of catalysis organized by the type of nucleophile involved in the process is reported.
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.
European Journal of Organic ChemistryAsymmetric Michael Additions to Nitroalkenes
834 Citations2002Otto Mathias Berner, Livio Tedeschi +1 more
ChemInformHighly Enantioselective Conjugate Addition of Nitromethane to Chalcones Using Bifunctional Cinchona Organocatalysts.
816 Citations2005Benedek Vakulya, Szilárd Varga +2 more
Chemical CommunicationsAsymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts
815 Citations2008Stephen J. Connon
Cinchona alkaloid derivatives modified to include a (thio)urea component have emerged in the last three years as readily accessible, robust and tunable bifunctional organocatalysts for a range of synthetically useful transformations.
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.
SynthesisOrganocatalytic Enantioselective Michael and Hetero-Michael Reactions
614 Citations2007José L. Vicário, Dolores Badı́a +1 more
Organic LettersEfficient Proline-Catalyzed Michael Additions of Unmodified Ketones to Nitro Olefins
587 Citations2001Benjamin List, Peter Pojarliev +1 more
This novel reaction provides gamma-nitro ketones in modest enantioselectivity yet excellent yields as well as proline-catalyzed Michael addition of unmodified ketones to nitro olefins.
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.
Chemical CommunicationsEnantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives
483 Citations2005Jinxing Ye, Darren J. Dixon +1 more
Thiourea derivative was identified as the most effective bifunctional organic catalyst and found to induce high enantioselectivity in the malonate ester Michael addition reaction to a range of nitro olefins.
Angewandte Chemie International EditionCatalytic Enantioselective Friedel–Crafts Alkylation of Indoles with Nitroalkenes by Using a Simple Thiourea Organocatalyst
460 Citations2005Raquel P. Herrera, Valentina Sgarzani +2 more
Journal of the American Chemical SocietyHighly Enantioselective Direct Conjugate Addition of Ketones to Nitroalkenes Promoted by A Chiral Primary Amine−Thiourea Catalyst
446 Citations2006Hongbing Huang, Eric N. Jacobsen
Broad substrate scope is described, with nitroalkenes bearing either aromatic or aliphatic substituents and a wide variety of ketones shown to be useful reacting partners.
Angewandte Chemie International EditionStereocontrolled Creation of Adjacent Quaternary and Tertiary Stereocenters by a Catalytic Conjugate Addition
399 Citations2004Hongming Li, Yi Wang +6 more
Angewandte Chemie International EditionA Chiral Primary Amine Thiourea Catalyst for the Highly Enantioselective Direct Conjugate Addition of α,α‐Disubstituted Aldehydes to Nitroalkenes
373 Citations2006Mathieu P. Lalonde, Yonggang Chen +1 more
Journal of the American Chemical SocietyA New Class of Chiral Pyrrolidine−Pyridine Conjugate Base Catalysts for Use in Asymmetric Michael Addition Reactions
357 Citations2004Takaaki Ishii, Shingo Fujioka +2 more
Direct catalytic asymmetric Michael addition reactions of ketones to nitroolefins using newly developed chiral pyrrolidine-pyridine conjugate bases as catalysts are described, obtaining the desired 1,4-adducts in excellent yields with high enantio- and diastereoselectivities.
Angewandte Chemie International EditionDirect, Highly Enantioselective Pyrrolidine Sulfonamide Catalyzed Michael Addition of Aldehydes to Nitrostyrenes
347 Citations2005Wei Wang, Jian Wang +1 more
Organic LettersDirect Asymmetric Organocatalytic Michael Reactions of α,α-Disubstituted Aldehydes with β-Nitrostyrenes for the Synthesis of Quaternary Carbon-Containing Products
322 Citations2004Nobuyuki Mase, Rajeswari Thayumanavan +2 more
Organic LettersHighly Enantioselective Construction of Spiro[<i>4H</i>-pyran-3,3′-oxindoles] Through a Domino Knoevenagel/Michael/Cyclization Sequence Catalyzed by Cupreine
302 Citations2010Wenbing Chen, Zhijun Wu +4 more
The first enantioselective organocatalytic two- and three-component reactions via a domino Knoevenagel/Michael/cyclization sequence with cupreine as catalyst have been developed and will provide promising candidates for chemical biology and drug discovery.
Bulletin of the Chemical Society of JapanDiscovery and Application of Asymmetric Reaction by Multi-Functional Thioureas
278 Citations2008Hideto Miyabe, Yoshiji Takemoto
It is discovered that bifunctional thiourea bearing a tertiary amino group signif...
Angewandte Chemie International EditionHighly Efficient Dynamic Kinetic Resolution of Azlactones by Urea‐Based Bifunctional Organocatalysts
263 Citations2005Albrecht Berkessel, Felix Cleemann +3 more
Journal of the American Chemical SocietyAxially Chiral Guanidine as Enantioselective Base Catalyst for 1,4-Addition Reaction of 1,3-Dicarbonyl Compounds with Conjugated Nitroalkenes
236 Citations2006Masahiro Terada, Hitoshi Ube +1 more
The axially chiral guanidine catalysts thus developed facilitated the highly enantioselective 1,4-addition reaction of 1,3-dicarbonyl compounds with a broad range of conjugated nitroalkenes and showed extremely high catalytic activity.
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.
Current Organic ChemistryChemistry of Aloe Species
233 Citations2000Ermias Dagne, Daniel Bisrat +2 more
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.
Advanced Synthesis & CatalysisGuanidine‐Thiourea Bifunctional Organocatalyst for the Asymmetric Henry (Nitroaldol) Reaction
218 Citations2005Yoshihiro Sohtome, Yuichi Hashimoto +1 more
Novel bifunctional catalysts having guanidine and thiourea functional groups were developed for the asymmetric Henry (nitroaldol) reaction and efficiently promoted the Henry reaction.
The Journal of Physical Chemistry CA Combined Experimental and Computational Investigation of Anthracene Based Sensitizers for DSSC: Comparison of Cyanoacrylic and Malonic Acid Electron Withdrawing Groups Binding onto the TiO<sub>2</sub> Anatase (101) Surface
206 Citations2009Kola Srinivas, Kada Yesudas +3 more
Chemical CommunicationsDirect enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative
204 Citations2006A. Louise Tillman, Jinxing Ye +1 more
Extension of this methodology to encompass the use of 2-substituted-1,3-dicarbonyl nucleophiles allows the formation of adjacent stereocentres, one of which is quaternary, in high relative and absolute stereocontrol.
Journal of the American Chemical SocietyChiral Bicyclic Guanidine-Catalyzed Enantioselective Reactions of Anthrones
191 Citations2006Juan Shen, Thanh-Truc Nguyen +5 more
This is the first case of a highly enantioselective base-catalyzed anthrone Diels-Alder reaction, and it was found that several anthrone derivatives suitable for this reaction were obtained.
ChemInformOrganocatalytic Asymmetric Michael Addition of 2,4‐Pentandione to Nitroolefins.
191 Citations2006Jian Wang, Hao Li +3 more
Angewandte Chemie International EditionCatalytic Asymmetric Conjugate Addition of Nitroalkanes to 4‐Nitro‐5‐styrylisoxazoles
153 Citations2009Andrea Baschieri, Luca Bernardi +3 more
Chemical CommunicationsSecond-generation organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones
141 Citations2005Albrecht Berkessel, Santanu Mukherjee +3 more
Bifunctional organocatalysts of the thiourea-tert-amine type, carrying two "matched" elements of chirality, effect the alcoholytic dynamic kinetic resolution of a variety of azlactones with up to 95% ee.
Advanced Synthesis & CatalysisOrganocatalytic Asymmetric Michael Addition of Pyrazolin‐5‐ones to Nitroolefins with Bifunctional Thiourea: Stereocontrolled Construction of Contiguous Quaternary and Tertiary Stereocenters
129 Citations2010Yu‐Hua Liao, Wenbing Chen +5 more
The first organocatalytic diastereo- and enantioselective Michael addition reaction of 4-substituted-pyrazolin-5-ones to nitroolefins has been developed with a chiral bifunctional thiourea as organoc atalyst.
Organic LettersHighly Diastereo- and Enantioselective Michael Additions of 3-Substituted Oxindoles to Maleimides Catalyzed by Chiral Bifunctional Thiourea−Tertiary Amine
121 Citations2010Yu‐Hua Liao, Xiong‐Li Liu +4 more
A highly diastereo- and enantioselective Michael addition reaction with respect to prochiral 3-substituted oxindoles and maleimides by a chiral bifunctional thiourea-tertiary amine catalyst was investigated for the first time.
The Journal of Organic ChemistryOrganocatalytic Enantioselective Hydroxymethylation of Oxindoles with Paraformaldehyde as C1 Unit
114 Citations2010Xiong‐Li Liu, Yu‐Hua Liao +4 more
A bifunctional thiourea-tertiary amine-catalyzed asymmetric hydroxymethylation of 3-substituted oxindoles using paraformaldehyde as the C1 unit was developed, which is activated by chiral bifunctionsal th iourea organocatalysts.
TetrahedronHighly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (−)-donaxaridine and (R)-chimonamidine
104 Citations2009Wenbing Chen, Xilin Du +3 more
Journal of the American Chemical SocietyThe Complete Gene Cluster of the Antitumor Agent Gilvocarcin V and Its Implication for the Biosynthesis of the Gilvocarcins
103 Citations2003Carsten Fischer, Fredilyn Lipata +1 more
This is the first reported gene cluster encoding the biosynthesis of a benzo[d]naphtho[1,2-b]pyran-6-one aryl C-glycoside antibiotic, which lays the foundation for the detailed studies of its intriguing biosynthetic steps and possibly for the generation of gilvocarcin analogues with improved biological activities through combinatorial biosynthesis.
European Journal of Organic ChemistrySugar‐Derived Bifunctional Thiourea Organocatalyzed Asymmetric Michael Addition of Acetylacetone to Nitroolefins
86 Citations2008Peng Gao, Chungui Wang +3 more
The Journal of Organic ChemistryOrganocatalytic Enantioselective Michael Addition of 2,4-Pentandione to Nitroalkenes Promoted by Bifunctional Thioureas with Central and Axial Chiral Elements
83 Citations2008Fangzhi Peng, Zhihui Shao +4 more
Two novel bifunctional amine-thiourea organocatalysts developed to promote enantioselective Michael reaction between 1,3-dicarbonyl compounds and nitro olefins afforded the desired products with good levels of enantiOSElectivity, showing clearly that two chiral elements of 2 are matched, and enhance the stereochemical control.
Journal of Medicinal ChemistryNovel Benzylidene-9(10<i>H</i>)-anthracenones as Highly Active Antimicrotubule Agents. Synthesis, Antiproliferative Activity, and Inhibition of Tubulin Polymerization
73 Citations2003Helge Prinz, Yukihito Ishii +10 more
The novel benzylidene-9(10H)-anthracenones described in the present study constitute an interesting group of highly active and easily accessible antimitotic agents that inhibit tubulin polymerization.
The Journal of Organic ChemistryMulticomponent Synthesis of Spiroisoxazolines
71 Citations2005Mauro F. A. Adamo, Donato Donati +2 more
A three-component one-pot procedure (3-MCR) was developed to assemble the spiroisoxazoline nucleus from commercially available materials and affords the title compounds in high yields and without the use of chromatography.
Angewandte Chemie International EditionHighly Enantioselective Catalytic Thiolysis of Prochiral Cyclic Dicarboxylic Anhydrides Utilizing a Bifunctional Chiral Sulfonamide
58 Citations2005Takashi Honjo, Shigeki Sano +2 more
Tetrahedron LettersA highly efficient asymmetric Michael addition of anthrone to nitroalkenes with cinchona organocatalysts
58 Citations2007Min Shi, Zhiyu Lei +2 more
Advanced Synthesis & CatalysisBifunctional Thiourea‐Catalyzed Asymmetric Addition of Anthrones to Maleimides
57 Citations2010Alex Zea, Guillem Valero +3 more
For the first time, the addition of anthrones to maleimides catalyzed by bifunctional thiourea catalysts is reported, furnishing the final Diels–Alder or Michael adducts in excellent yields and enantioselectivities.
Organic LettersMulticomponent Synthesis of 3-Indolepropionic Acids
54 Citations2006Mauro F. A. Adamo, Vivekananda R. Konda
A three-component one-pot procedure (3-MC) was developed to assemble 3-indolepropionic acids from commercially available materials in high yields and without the use of chromatography.
Chemistry - A European JournalConstruction of Helical J‐Aggregates Self‐Assembled from a Thymidylic Acid Appended Anthracene Dye and DNA as a Template
53 Citations2009Rika Iwaura, Mayumi Ohnishi‐Kameyama +1 more
It is concluded that thymine-adenine base-pair formation induced supramolecular helical J-aggregates in the binary self-assembly of 1 and dA(20) in aqueous solutions.
TetrahedronModular synthesis of isoxazolopyridones and pyrazolopyridones
49 Citations2006Mauro F. A. Adamo, Eleanor F. Duffy +2 more
The Journal of Organic ChemistryStructure−Property Relationships in Conjugated Donor−Acceptor Molecules Based on Cyanoanthracene: Computational and Experimental Studies
49 Citations2005Jui-Hsien Lin, Arumugasamy Elangovan +1 more
Two series of pi-conjugated bipolar compounds, namely, 9-phenyl-10-anthronitriles (PAN and PEAN series), having inherent redox centers have been synthesized and their electronic absorption, fluorescence emission, and electrochemical behavior have been studied.
Advanced Synthesis & CatalysisDevelopment of a Mild Procedure for the Addition of Bisulfite to Electrophilic Olefins
45 Citations2010Francesco Fini, Murali Nagabelli +1 more
Journal of the Chemical Society Perkin Transactions 1Asymmetric cycloaddition of anthrone and maleimides catalyzed by C2-chiral pyrrolidines
44 Citations2001Kouhei Uemae, Satoshi Masuda +1 more
European Journal of Organic ChemistryA First Case of Asymmetric Catalysis Induced by Metal‐Free Bisoxazolines
44 Citations2008Deniz Akalay, Gerd Dürner +1 more
TetrahedronModular syntheses of isoxazoloazepinones and pyrazoloazepinones
41 Citations2007Mauro F. A. Adamo, Eleanor F. Duffy +2 more
Tetrahedron AsymmetryAsymmetric cycloaddition of anthrone with N-substituted maleimides with C2-chiral pyrrolidines
38 Citations1997Kyohei Tokioka, Satoshi Masuda +3 more
PubMedMechanism of mouse skin tumor promotion by chrysarobin.
36 Citations1985John DiGiovanni, Patricia C. Decina +4 more
The hypothesis that anthracene-derived skin tumor promoters work at least in part by a mechanism different from the phorbol esters is supported.
Tetrahedron AsymmetryEnantioselective Michael addition of anthrone to nitroalkenes catalyzed by bifunctional thiourea-tertiary amines
35 Citations2009Yu‐Hua Liao, Hui Zhang +4 more
A highly bifunctional thiourea-tertiary amine-catalyzed enantioselective Michael addition reaction of anthrone to a wide variety of nitroalkenes has been developed, and the corresponding adducts were obtained smoothly in high yields and good enantiOSElectivities.
HeterocyclesAn Improved Synthesis of 3-Methyl-4-nitro-5-heteroarylethenylisoxazoles
31 Citations2007Mauro F. A. Adamo, Eleanor F. Duffy +2 more
Journal of Medicinal ChemistryAntipsoriatic Anthrones with Modulated Redox Properties. 4. Synthesis and Biological Activity of Novel 9,10-Dihydro-1,8-dihydroxy-9-oxo-2- anthracenecarboxylic and -hydroxamic Acids
29 Citations1997Klaus Müller, Helge Prinz
Contrary to anthralin, antioxidant properties were observed as documented by the reactivity of the novel compounds against free radicals and inhibition of lipid peroxidation in model membranes.
Tetrahedron LettersEnantioselective addition of anthrones to α,β-unsaturated aldehydes
26 Citations2009Andrea‐Nekane R. Alba, Natalia Bravo +2 more
Chemical and Pharmaceutical BulletinStudies on Anthracenes. 1. Human Telomerase Inhibition and Lipid Peroxidation of 9-Acyloxy 1,5-Dichloroanthracene Derivatives.
25 Citations2001Hsu‐Shan Huang, Jing‐Min Hwang +5 more
In an attempt to understand the mechanism of how anthracenone achieves desirable selectivity, solid-state structures of anthracene derivatives have been obtained and their ability to inhibit the telomere-addition function of the human telomerase enzyme was determined.
Organic & Biomolecular ChemistryAsymmetric organocatalytic Michael addition of anthrone to enone
22 Citations2010Chunlin Wu, Wenjun Li +3 more
Archiv der PharmazieSynthesis and Cytotoxicity of 9-Alkoxy-1, 5-dichloroanthracene Derivatives in Murine and Human Cultured Tumor Cells
17 Citations2002Hsu‐Shan Huang, Jeng‐Fong Chiou +3 more
9‐Alkoxy‐1, 5‐dichloroanthracenes were sucessfully prepared and cytotoxicity was evaluated in vitro on rat glioma C6 cell lines and human hepatoma G2 cell lines, respectively, showing potent cytotoxins among these compounds.
Australian Journal of ChemistrySynthesis of the Androgen-Receptor Antagonists (±)-Ws9761 A and B
12 Citations1996DW Cameron, C. E. SKENE
Letters in Organic ChemistryChiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective 1,4- Conjugate Addition of &#946;-Ketoesters to Nitroolefins
6 Citations2010Hui Zhang, Linfeng Cun +2 more
…