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周剑

  华东师范大学化学系,教授、博士导师。
 

  获奖情况:
  2011        “Thieme Chemistry Journals 2011 Award”
  2006    “全国百篇优秀博士论文”提名奖
  2005    “中国科学院2005年50篇优秀博士论文”奖
  1996    四川省十佳大学生

 

  学术简介
  周剑教授多年来一直从事不对称催化方向的研究工作,在手性金属催化和有机小分子催化两方面具有较好的研究基础。独立工作前在J. Am. Chem. Soc.; Angew. Chem. Int. Ed.等国际著名期刊上发表21篇论文(包括JACS两篇,AGIE四篇),他引八百多次。其中包括一篇Angew. Chem. Int. Ed.封面文章,VIP文章;一篇Chem. Soc. Rev. 封面文章。第一作者文章有两篇他引次数超过100次,最高达132次,另有三篇文章他引次数超过50。
  自2008年11月独立工作以来已经在J. Am. Chem. Soc.; Angew. Chem. Int. Ed.; Chem. Sci.等国际著名期刊上正式接受和发表十多篇SCI文章, 他引100多次。研究方向是新型手性催化剂的设计开发,以绿色合成化学为导向的不对称催化的新反应开发和应用及其在具有生物活性的天然产物及药物分子的合成应用研究。目前主持一项国家自然科学基金青年基金项目一项面上项目,入选上海市“浦江计划”,并参与一项国家973项目研究。

 

  目前主要开展两方面的研究工作:
  一是“废弃物作为催化剂”的串联反应设计策略的应用研究。我们率先提出利用该策略,改善一些原子经济性较低的反应的利用率。通过把产生大量废弃物的反应模块化组合到串联反应中,直接利用这些废弃物作为下一步反应的催化剂,从而改善总体的原子利用率。利用该策略,我们设计开发了两个新型串联反应:Wittig-共轭还原反应以及Wittig-羟腈化反应,直接利用Wittig反应产生的三苯氧膦作为下一步反应的催化剂,初步研究成果已经在Angew. Chem. Int. Ed.上发表。
  二是具有四取代碳手性中心的不对称催化构建。具有四取代碳手性中心的结构单元在天然产物分子和药物分子中大量存在,发展高效的合成方法快速构建这类结构单元,有助于合成相关天然产物分子和药物分子及其类似物,研究结构和性质的相互关系,加快新药开发。从合成化学角度来看,四取代碳手性中心的不对称催化构建从电子效应和立体效应来讲都具有很大的挑战性,是不对称催化领域的前沿热点和难点领域之一。我们着重于具有C3位四取代碳手性中心的氧化吲哚结构单元和含氟烷基取代的季碳原子的不对称催化构建,以发展新的催化理念和开发新的催化体系为目标,并力图应用我们自己的方法于相关天然产物分子的全合成研究。目前已经在J. Am. Chem. Soc.; Chem. Sci.; Chem. Commun.; Org. Lett.; Adv. Synth. Catal.; Org. Biomol. Chem.等国际著名杂志上发表一些初步研究成果。

 

  独立工作以来发表的文章(自2008年11月加入华东师范大学):
  12) F. Zhou, Z.-Y. Cao, J. Zhang, H. B. Yang, J. Zhou,* A Highly Efficient Friedel-Crafts Reaction of 3-Hydroxyoxindoles and Aromatic Compounds to 3,3-Diaryl and 3-Alkyl-3-aryloxindoles Catalyzed by Hg(ClO4)2?3H2O. Chem. Asian J.2011, in press.


  11) C.-B. Ji, Y.-L.Liu, Z.-Y.Cao, Y.-Y.Zhang, J. Zhou* Hydroxymethylation of α-substituted nitroacetates.Tetrahedron Lett.2011, 40, 6118-6121.


  10) F. Zhou, M. Ding, Y.-L. Liu,a C.-H. Wang, C.-B.Ji, Y.-Y.Zhang; J. Zhou* Organocatalytic Asymmetric α-Amination of Unprotected 3-Aryl and 3-Aliphatic Substituted Oxindoles Using Di-tert-butyl Azodicarboxylate.Adv. Syn. Catal.2011, 353, in press.


  9) M. Ding, F. Zhou, Y.-L.Liu, C.-H.Wang, X.-L. Zhao, J. Zhou,* Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins. Chem. Sci. 2011, 2, 2035. (Highlighted by Synfact 2011, 1245)


  8) Y.-L. Liu, T.-D.Shi, F. Zhou, X.-L.Zhao, X. Wang,* J. Zhou,* Organocatalytic Asymmetric Strecker Reaction of Di- and Trifluoromethyl Ketoimines.Remarkable Fluorine EffectOrg. Lett.2011, 13, 3826-3829. (Highlighted by Synfact 2011, 1015)


  7)Y.-L. Liu, B.-L.Wang, J.-J.Cao, L. Chen, Y.-X.Zhang, C. Wang, J. Zhou,* Organocatalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-oxindoles via Morita?Baylis?Hillman Reaction.J. Am. Chem. Soc. 2010, 132, 15176.(Highlighted by Synfact 2010, 1422)
 

  6) Y.-L. Liu, F. Zhou, J.-J.Cao, C.-B. Ji, M. Ding, J. Zhou,* A facile method for the synthesis of oxindole based quaternary α-aminonitriles via the Strecker reactionOrg. Biomol. Chem.2010, 8, 3847-3850. (本文为封面文章)


  5)J.-J. Cao, F. Zhou, J. Zhou,* Improving the Atom Efficiency of the Wittig Reaction by a “Waste as Catalyst/Co-catalyst” Strategy (pages 4976–4980). Angew. Chem. Int. Ed.2010, 49, 4976-4980.


  4) F. Zhou, Y.-L.Liu, J. Zhou,* Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C-3 Position (pages 1381–1407).Adv. Syn. Catal.2010, 352, 1381-1407.


  3)M. Ding, F. Zhou, Z.-Q.Qian, J. Zhou,* Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins.Org. Biomol. Chem.2010, 8, 2912-1914.


  2) J. Zhou,* Recent Advances in Multicatalyst Promoted Asymmetric Tandem Reactions (pages 422–434)Chem. Asian J.2010, 4,422-434.


  1) Z.-Q. Qian, F. Zhou, T.-P.Du, M. Ding, B.-L.Wang, X.-L.Zhao, J. Zhou,* Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of 3-substituted oxindolesChem. Commun.2009, 6753-6755.


  独立工作以前发表的代表性文章
  1) J. Zhou, V. Wakchaure, P. Krafft, B. List, Primary Amine-Catalyzed Enantioselective Intramolecular Adolizations. Angew. Chem. Int. Ed.2008, 46, 7656-7658. (本文为封面文章,VIP文章).


  2) J. Zhou, B. List, Organocatalytic Asymmetric Reaction Cascade to Substituted Cyclohexylamines. J. Am. Chem. Soc. 2007, 129, 7498-7499。 (本文入选2007年JACS第二季度“most accessed articles”)


  3)  J. Zhou, Y. Tang, Sidearm Effect: Improvement of the Enantiomeric Excess in the Asymmetric Michael Addition of Indoles to Alkylidene Malonates. J. Am. Chem. Soc.2002, 124, 9030-9031.


  4) J. Zhou, Y. Tang, The development and application of chiral trisoxazolines in asymmetric catalysis and molecular recognition. Chem. Soc. Rev. 2005, 34, 644-676. (本文为封面文章).


  5) L.-W. Ye, J. Zhou, Y. Tang, Phosphine-triggered synthesis of functionalized cyclic compounds. Chem. Soc. Rev. 2008, 37, 1140-1152.
 

  6)S. C. Pan, J. Zhou, B. List, Catalytic Asymmetric Acylcyanation of Imines. Angew. Chem. Int. Ed. 2007, 45, 612-614.


  7) W. Schrader, P. P. Handayani, J. Zhou, B. List, Characterization of Key Intermediates in a Complex Organocatalytic Cascade Reaction Using Mass Spectrometry. Angew. Chem. Int. Ed.2009, 48, 1463-1466.


  8) V. Wakchaure, J. Zhou, S. Hoffmann, B. List, Catalytic Asymmetric Reductive Amination of a-Branched Ketones. Angew. Chem. Int. Ed.2010, 49, 4612-4614.


  9)  J.Zhou, Y. Tang, Enantioselective Friedel–Crafts reaction of indoles with arylidene malonates catalyzed by iPr-bisoxazoline–Cu(OTf)2.Chem. Commun.2004, 432-433.


  10) J. Zhou, M.-C.Ye, Z.-Z. Huang, Y. Tang, Controllable Enantioselective Friedel-Crafts Reaction between Indoles and Alkylidene Malonates Catalyzed by Pseudo-C3-Symmetric Trisoxazoline Copper (II) Complexes. J. Org. Chem.2004, 69, 1309-1320.


  11) J. Zhou, M.-C. Ye, Y. Tang, Sidearm Approach: A Promising Strategy for Construction of Bisoxazoline-Based Ligand Library. J. Comb. Chem.2004, 6, 301-304.


  12) J. Zhou, Y. Tang, Pseudo-C3-symmetric trisoxazolines as ligands in copper catalyzed enantioselective Diels–Alder reaction. Org. Biomol. Chem.2004, 2, 429-433.


  13) J. Zhou, B. List, Synthesis of trans-3-Substituted Cyclohexylamines via Br?nsted Acid Catalyzed and Substrate-Mediated Triple Organocatalytic Cascade Reaction. Synlett2007, 2037-2040.


  14) M.-C. Ye, J. Zhou, Z.-Z. Huang, Y. Tang, Chiral tris(oxazoline)/Cu(II) catalyzed coupling of terminal alkynes and nitrones. Chem. Commun.2003, 2554-2555. [被Angew. Chem. Int. Ed. 的Highlights 栏目评述 (Angew. Chem. Int. Ed.2004, 43, 2198.)].


  15) M.-C. Ye, J. Zhou, X.-L. Sun, Y. Tang, Trisoxazoline/Cu(II)-Promoted Kinugasa Reaction Enantioselective Synthesis of Lactams. J. Org. Chem.2006, 71, 3576-3582.


  16) S. C. Pan, J. Zhou, B. List, Catalytic Acylcyanation of Imines with Acetylcyanide. Synlett2006, 3275-3276.


  17) Z.-Z. Huang, Y. B. Kang, J. Zhou, M.-C. Ye, Y. Tang, Diastereoselectivity-Switchable and Highly Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to Alkylidene Malonate. Org. Lett.2004, 6, 1677-1679.


  18) M.-C. Ye, B. Li, J. Zhou, X.-L. Sun, Y. Tang, Modular Synthesis of Chiral Homo- and Heterotrisoxazolines.Improving the Enantioselectivity in the Asymmetric Michael Addition of Indole to Benzylidene Malonate. J. Org. Chem. 2005, 70, 6108-6110. (本文被Synfact收录, Synfacts, 2005, 203).


  19) J.-P. Qiu, Z.-H.Xu, J. Zhou, C.-L.Cao, X.-L.Sun, L.-X. Dai, Y. Tang, Ligand-Accelerated Asymmetric [1,2]-Stevens Rearrangment of Sulfur Ylides via Decomposition of Diazomalonates Catalyzed by Chiral Bisoxazoline/Copper Complex. Adv. Syn. Catal.2009, 351, 308-312.


  20) C.-L. Cao, Y.-Y.Zhou, J. Zhou, X.-L.Sun, Y. Tang, Y.-X.Li, G.-Y. Li, J. Sun, An orgaonocatlaytic tandem reaction for the construction of bicyclic skeletons. Chem. Eur. J.2009, 15, 11384-11389.


  21)  J.-P. Qiu, C. Deng, J. Zhou, X.-L. Sun, Y. Tang, Switchable Reactions of Cyclopropanes with Enol Silyl Ethers. Controllable Synthesis of Cyclopentanes and 1,6-Dicarbonyl Compounds. J. Org. Chem. 2009, 74, 7684-7689.

 

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