Citation: Qing-Fang Cheng, Jing-Wen Wang, Qi-Fa Wang, Zhou Liu. Intermolecular Stetter reaction of aromatic aldehydes with (E)-(2-nitrovinyl)cyclohexane induced by N-heterocyclic carbene and thiourea[J]. Chinese Chemical Letters, ;2016, 27(7): 1032-1035. doi: 10.1016/j.cclet.2016.03.007 shu

Intermolecular Stetter reaction of aromatic aldehydes with (E)-(2-nitrovinyl)cyclohexane induced by N-heterocyclic carbene and thiourea

  • Corresponding author: Qi-Fa Wang, hmahdavinia@gmail.com
  • Received Date: 10 December 2015
    Revised Date: 24 February 2016
    Accepted Date: 1 March 2016
    Available Online: 14 July 2016

Figures(2)

  • Intermolecular Stetter reaction of aromatic aldehydes with (E)-(2-nitrovinyl)cyclohexane catalyzed by thiazolium A has been developed. The reaction rate and efficiency are profoundly impacted by the presence of thiourea B. The reaction affords moderate to good yields of the Stetter product. Some factors influencing yield were discussed.
  • 加载中
    1. [1]

      H. Stetter, M. Schreckenberg. A new method for addition of aldehydes to activated double bonds[J]. Angew. Chem. Int. Ed. Engl., 1973,1281.  

    2. [2]

      H. Stetter. Catalyzed addition of aldehydes to activated double bonds—a new synthetic approach[J]. Angew. Chem. Int. Ed., 1976,15:639-640. doi: 10.1002/(ISSN)1521-3773

    3. [3]

      M. Christmann. New developments in the asymmetric Stetter reaction[J]. Angew. Chem. Int. Ed., 2005,44:2632-2634. doi: 10.1002/(ISSN)1521-3773

    4. [4]

      D. Enders, K. Breuer, J. Runsink. The first asymmetric intramolecular Stetter reaction[J]. Helv. Chim. Acta., 1996,79:1899-1902. doi: 10.1002/(ISSN)1522-2675

    5. [5]

      M.S. Kerr, J.R. de Alaniz, T. Rovis. A highly enantioselective catalytic intramolecular Stetter reaction[J]. J. Am. Chem. Soc., 2002,124:10298-10299. doi: 10.1021/ja027411v

    6. [6]

      C.C. Steven, T. Rovis. Catalytic asymmetric Stetter reaction onto vinylphosphine oxides and vinylphosphonates[J]. Org. Lett., 2008,10:3141-3144. doi: 10.1021/ol801047k

    7. [7]

      J.R. de Alaniz, M.S. Kerr, J.L. Moore, T. Rovis. Scope of the asymmetric intramolecular Stetter reaction catalyzed by chiral nucleophilic triazolinylidene carbenes[J]. J. Org. Chem., 2008,73:2033-2040. doi: 10.1021/jo702313f

    8. [8]

      J.R. de Alaniz, T. Rovis. A highly enantio- and diastereoselective catalytic intramolecular Stetter reaction[J]. J. Am. Chem. Soc., 2005,127:6284-6289. doi: 10.1021/ja0425132

    9. [9]

      S.M. Mennen, J.T. Blank, M.B. Tran-Dube, J.E. Imbriglio, S.J. Miller, A peptidecatalyzed asymmetric Stetter reaction, Chem. Commun.41 (2005) 195-197.

    10. [10]

      A.E. Mattson, A.R. Bharadwaj, K.A. Scheidt. The thiazolium-catalyzed sila-Stetter reaction: conjugate addition of acylsilanes to unsaturated esters and ketones[J]. J. Am. Chem. Soc., 2004,126:2314-2315. doi: 10.1021/ja0318380

    11. [11]

      X.L. Hu, J.S. Johnson. Kinetic control in direct α-silyloxy ketone synthesis: a new regiospecific catalyzed cross silyl benzoin reaction[J]. Angew. Chem., 2003,115:2638-2640. doi: 10.1002/ange.200250554

    12. [12]

      Q. Liu, S. Perreault, T. Rovis. Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates[J]. J. Am. Chem. Soc., 2008,130:14066-14067. doi: 10.1021/ja805680z

    13. [13]

      D. Enders, J.W. Han, A. Henseler. Asymmetric intermolecular Stetter reactions catalyzed by a novel triazolium derived N-heterocyclic carbene[J]. Chem. Commun., 2008,44:3989-3991.  

    14. [14]

      J.M. Zhang, C. Xing, B. Tiwari, Y.G.R. Chi. Catalytic activation of carbohydrates as formaldehyde equivalents for Stetter reaction with enones[J]. J. Am. Chem. Soc., 2013,135:8113-8116. doi: 10.1021/ja401511r

    15. [15]

      D.A. DiRocco, K.M. Oberg, D.M. Dalton, T. Rovis. Catalytic asymmetric intermolecular Stetter reaction of heterocyclic aldehydes with nitroalkenes: backbone fluorination improves selectivity[J]. J. Am. Chem. Soc., 2009,131:10872-10874. doi: 10.1021/ja904375q

    16. [16]

      D.A. DiRocco, T. Rovis. Catalytic asymmetric intermolecular Stetter reaction of enals with nitroalkenes: enhancement of catalytic efficiency through bifunctional additives[J]. J. Am. Chem. Soc., 2011,133:10402-10405. doi: 10.1021/ja203810b

    17. [17]

      A.E. Mattson, A.M. Zuhl, T.E. Reynolds, K.A. Scheidt. Direct nucleophilic acylation of nitroalkenes promoted by a fluoride anion/thiourea combination[J]. J. Am. Chem. Soc., 2006,128:4932-4933. doi: 10.1021/ja056565i

    18. [18]

      G.C. Vougioukalakis, R.H. Grubbs. Synthesis and activity of ruthenium olefin metathesis catalysts coordinated with thiazol-2-ylidene ligands[J]. J. Am. Chem. Soc., 2008,130:2234-2245. doi: 10.1021/ja075849v

    19. [19]

      J. Wang, H. Li, W. Duan. Organocatalytic asymmetric Michael addition of, 2, 4-pentandione to nitroolefins[J]. Org. Lett., 2005,7:4713-4716. doi: 10.1021/ol0519137

    20. [20]

      T. Okino, Y. Hoashi, T. Furukawa. Enantio- and diastereoselective Michael reaction of, 1, 3-dicarbonyl copounds to nitroolefins catalyzed by a bifunctional thiourea[J]. J. Am. Chem. Soc., 2005,127:119-125. doi: 10.1021/ja044370p

    21. [21]

      C.J. Wang, Z.H. Zhang, X.Q. Dong. Chiral amine-thiourea bearing multiple hydrogen bonding donors: highly efficient organocatalysts for asymmetric Michael addition of acetylacetone to nitroolefins[J]. Chem. Commun., 2008,44:1431-1433.  

  • 加载中
    1. [1]

      Bo Han Wei Huang Zhen Rui Xu Xiao Ping Dong . Asymmetric aza-Henry reaction with α-substituted nitroacetates catalyzed by a bifunctional thiourea-guanidine catalyst. Chinese Chemical Letters, 2011, 22(8): 923-926. doi: 10.1016/j.cclet.2011.01.038

    2. [2]

      Hui Chen Ru Jiang Qiao Feng Wang Xiao Li Sun Jing Luo Sheng Yong Zhang . Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed “interrupted” Feist-Bénary reaction. Chinese Chemical Letters, 2010, 21(2): 167-170. doi: 10.1016/j.cclet.2009.10.012

    3. [3]

      Li Tian Jie Song Jing Wang Bin Liu . Synthesis and bioactivity of N-cyclopropanecarboxyl-N'-pyridin-2-yl thiourea derivatives and related fused ring compounds. Chinese Chemical Letters, 2009, 20(3): 288-291. doi: 10.1016/j.cclet.2008.11.027

    4. [4]

      Ge MengMei-Lin ZhengA-Qun ZhengMei WangaJuan Shi . The novel usage of thiourea nitrate in aryl nitration. Chinese Chemical Letters, 2014, 25(1): 87-89.

    5. [5]

      Mohammad Hossein MashhadizadehRasoul Pourtaghavi Talemi . Application of diazo-thiourea and gold nano-particles in the design of a highly sensitive and selective DNA biosensor. Chinese Chemical Letters, 2015, 26(1): 160-166. doi: 10.1016/j.cclet.2014.09.004

    6. [6]

      Ning Ning Wan Yong Lei Yang Wen Ping Wang Zheng Feng Xie Ji De Wang . Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by Cu(Ⅱ)-imine complex. Chinese Chemical Letters, 2011, 22(10): 1155-1158. doi: 10.1016/j.cclet.2011.04.013

    7. [7]

      KHATOON SuraiyaNAQVI Andleeb Z. . Nonelectrolyte-Induced CP Variation of TX-114+TBAB System. Acta Physico-Chimica Sinica, 2008, 24(07): 1180-1184. doi: 10.1016/S1872-1508(08)60052-2

    8. [8]

      Dong-Ju ZhouLi-Bo DaiHui NiGen-Lei HuiSi-Guo Yuan . Preparation and characterization of polyphenylene sulfide-based chelating fibers. Chinese Chemical Letters, 2014, 25(2): 221-225.

    9. [9]

      Li Jun Yan Quan Zhong Liu Xue Lian Wang . Novel chiral thioureas for highly enantioselective Michael reactions of malonates to nitroalkenes. Chinese Chemical Letters, 2009, 20(3): 310-313. doi: 10.1016/j.cclet.2008.11.021

    10. [10]

      Miao-Miao Hong Ai-Feng Liu Ying Xu Dong-Mei Xu . Synthesis and properties of three novel rhodamine-based fluorescent sensors for Hg2+. Chinese Chemical Letters, 2016, 27(6): 989-992. doi: 10.1016/j.cclet.2016.03.027

    11. [11]

      Xiao Ming JI He Ping SUN Hai Wei XU Hong Min LIU . Synthesis of New Thiazine and Thiosemicarbazone Derivatives from D-Xylose. Chinese Chemical Letters, 2006, 17(12): 1563-1565.

    12. [12]

      Ye Hai-MuHong Liu-TingGao YangXu Jun . Isomorphism in ternary complex: Poly (ethylene oxide), urea and thiourea. Chinese Chemical Letters, 2017, 28(4): 888-892. doi: 10.1016/j.cclet.2016.12.032

    13. [13]

      Xi Li-LiMa Hong-BingTao Guan-Hong . Thiourea functionalized CdSe/CdS quantum dots as a fluorescent sensor for mercury ion detection. Chinese Chemical Letters, 2016, 27(9): 1531-1536. doi: 10.1016/j.cclet.2016.03.002

    14. [14]

      Lin HeHao GuoXiao-Wei MaJie ZhangCheng-Zhi GuWei WangBin DaiN-Heterocyclic carbene-catalyzed synthesis of acetyltributylcitrate via a transesterification reaction. Chinese Chemical Letters, 2014, 25(2): 215-217.

    15. [15]

      Wang YangLan Yu . Mechanism and origin of diastereoselectivity of N-heterocyclic carbene-catalyzed cross-benzoin reaction: A DFT study. Chinese Chemical Letters, 2020, 31(3): 736-738. doi: 10.1016/j.cclet.2019.08.010

    16. [16]

      Kong Yong . Research Advances of N-Heterocyclic Carbene Ligands in Polymerization. Chemistry, 2020, 83(9): 792-798.

    17. [17]

      Lei DaiSong Ye . Recent advances in N-heterocyclic carbene-catalyzed radical reactions. Chinese Chemical Letters, 2021, 32(2): 660-667. doi: 10.1016/j.cclet.2020.08.027

    18. [18]

      LIU JunHUO RanWEI QingZHAO Zhi-XiangLIU qing-Xiang . Synthesis and Structural Study of a N-Heterocyclic Carbene Trinuclear Silver(I) Complex. Chinese Journal of Structural Chemistry, 2016, 35(2): 313-318. doi: 10.14102/j.cnki.0254-5861.2011-0818

    19. [19]

      LIU JunHUO RanWEI QingZHAO Zhi-XiangLIU qing-Xiang . Synthesis and Structural Study of a N-Heterocyclic Carbene Trinuclear Silver(I) Complex. Chinese Journal of Structural Chemistry, 2016, 35(2): 313-318. doi: 10.14102/j.cnki.0254-5861.2011-0818

Metrics
  • PDF Downloads(0)
  • Abstract views(198)
  • HTML views(2)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return