Citation: Jie-Xiong Wang, Jing-Jing Wu, Heng Chen, Shao-Wu Zhang, Fan-Hong Wu. Synthesis of difluoroalkyl-γ-butyrolactones from iododifluoromethyl ketones and 4-pentenoic acids[J]. Chinese Chemical Letters, ;2015, 26(11): 1381-1384. doi: 10.1016/j.cclet.2015.07.007 shu

Synthesis of difluoroalkyl-γ-butyrolactones from iododifluoromethyl ketones and 4-pentenoic acids

  • Corresponding author: Jing-Jing Wu,  Fan-Hong Wu, 
  • Received Date: 4 May 2015
    Available Online: 24 June 2015

  • A convenient and efficient approach for difluoroalkyl-containing γ-butyrolactones via the radical addition reaction of iododifluoromethyl ketones with 4-pentenoic acids initiated by AIBN in CH3CN at 60 ℃ was reported. Various difluoroalkyl-containing δ-valerolactones were also synthesized under this reaction conditions.
  • 加载中
    1. [1]

      [1] R.P. Tripathi, B. Singh, S.S. Bisht, J. Pnadey, L-Ascorbic acid in organic synthesis: an overview, Curr. Org. Chem. 13 (2009) 99-122.

    2. [2]

      [2] C. Wang, G.A. Russell, γ-Lactone formation in the addition of benzenesulfonyl bromide to diene and enyne esters, J. Org. Chem. 64 (1999) 2066-2069.

    3. [3]

      [3] G.R. Flematti, E.L. Ghisalberti, K.W. Dixon, R.D. Trengove, A compound from smoke that promotes seed germination, Science 305 (2004), 977.

    4. [4]

      [4] C. Meier, T. Knispel, V.E. Marquez, et al., Cyclosal-pro-nucleotides of 2'-fluoro-araand 2'-fluoro-ribo-2',3'-dideoxyadenosine (F-ara- and F-ribo-ddA) as a strategy to bypass a metabolic blockade, J. Med. Chem. 42 (1999) 1615-1624.

    5. [5]

      [5] M.A. Zeller, M. Riener, D.A. Nicewicz, Butyrolactone synthesis via polar radical crossover cycloaddition reactions: diastereoselective syntheses of methylenolactocin and protolichesterinic acid, Org. Lett. 18 (2014) 4810-4813.

    6. [6]

      [6] T.P. Montgomery, A.H. Boyoung, Y. Park, M.J. Krische, Enantioselective conversion of primary alcohols to α-exo-Methylene γ-butyrolactones via iridium-catalyzed C-C bond-forming transfer hydrogenation: 2-(alkoxycarbonyl)allylation, J. Am. Chem. Soc. 27 (2012) 11100-11103.

    7. [7]

      [7] S. Li, S. Ma, Highly selective nickel-catalyzed methyl-carboxylation of homopropargylic alcohols for α-alkylidene-γ-butyrolactones, Org. Lett. 22 (2011) 6046- 6049.

    8. [8]

      [8] T.M. Lv, F.H. Wu, Progress in selective iodolactonization, Chin. J. Org. Chem. 8 (2003) 763-769.

    9. [9]

      [9] M. Zhu, L. Li, J.Y. Tang, H. Zhang, An effective method for the preparation of chlorolactones, Chin. Chem. Lett. 4 (2011) 431-434.

    10. [10]

      [10] B.E. Smart, Fluorine substituent effects on bioactivity, J. Fluorine Chem. 109 (2007) 3-11.

    11. [11]

      [11] S. Purser, P.R. Moore, S. Swallow, V. Gouverneur, Fluorine in medicinal chemistry, Chem. Soc. Rev. 37 (2008) 320-330.

    12. [12]

      [12] X.Y. Jiang, X.H. Xu, F.L. Qing, Design and concise synthesis of gem-difluormethylenated analogue of 7-epi-castanospermine, Chin. Chem. Lett. 8 (2014) 1115- 1120.

    13. [13]

      [13] W. Gu, J. Lin, J. Xiao, Direct N-gem-difluorocyclopropylation of nitro-heterocycles by utilizing gem-difluorocyclopropyl tosylate, Chin. Chem. Lett. 24 (2014) 24-28.

    14. [14]

      [14] C. Lu, Y.L. Shi, Z. Zhou, et al., Perfluorinated compounds in blood of textile workers and barbers, Chin. Chem. Lett. 25 (2014) 1145-1148.

    15. [15]

      [15] H. Xiao, H.Y. Duan, R.S. Yao, et al., Chemoselective synthesis of trifluoromethylated γ-butenolide derivatives via phosphine-promoted tandem reaction of allylic carbonates and trifluoromethyl ketones, Org. Lett. 20 (2014) 5462-5465.

    16. [16]

      [16] Y. Xiong, Z.H. Ju, X.G. Wang, X. Fang, F.H. Wu, Progress in the synthetic methods of fluorine-containing lactones, Chin. J. Org. Chem. 11 (2009) 1728-1743.

    17. [17]

      [17] P. Bravo, M. Frigerio, A. Melloni, et al., Stereoselective synthesis of both enantiomers of trifluoro-γ-valerolactone and pentafluoro-γ-caprolactone, Eur. J. Org. Chem. (2002) 1895-1902.

    18. [18]

      [18] K. Tenza, J.S. Northen, D. O'Hangan, A.M.Z. Slawin, Stereoselective α-fluoroamide and a-fluoro-γ-lactone synthesis by an asymmetric zwitterionic aza-claisen rearrangement, Beilstein J. Org. Chem. 13 (2005) 13-17.

    19. [19]

      [19] M. Tredwell, J.A.R. Luft, M. Schuler, et al., Fluorine-directed diastereoselective iodocyclizations, Angew. Chem. Int. Ed. 2 (2008) 357-360.

    20. [20]

      [20] A. Chatupheeraphat, D. Soorukram, C. Kuhakarn, et al., Synthesis of gem-difluoromethylenated spiro-γ-butyrolactones by employing PhSCF2Si(CH3)3 as a gemdifluoromethylenating agent, Eur. J. Org. Chem. (2013) 6844-6858.

    21. [21]

      [21] H.F. Cui, Z. Chai, Y.P. Lu, et al., Direct double electrophilic fluorination of allenoic acids and tosylamides to give 1,1-difluoroallylic heterocyclic compounds, Chin. J. Chem. 29 (2011) 2744-2748.

    22. [22]

      [22] X. Fang, Q. Ying, Y. Chen, et al., Synthesis of fluoroalkyl-δ-lactones from polyfluoroalkyl iodides and 5-hexenoic acids, J. Fluorine Chem. 128 (2008) 280-285.

    23. [23]

      [23] X.W. Zou, F.H. Wu, A convenient method of polyfluoroalkyl-lactonization, Chin.Chem. Lett. 13 (2002) 410-411.

    24. [24]

      [24] F.H. Xiao, F.H. Wu, X.Y. Yang, Y.J. Shen, X.M. Shi, A convenient synthesis of fluoroalkylated γ-butyrolactones from polyfluoroalkyl iodides and 4-pentenoic acid catalyzed by Pd(PPh3)4, J. Fluorine Chem. 126 (2005) 319-323.

    25. [25]

      [25] I. Saidalimu, X. Fang, X.P. He, et al., Highly hnantioselective construction of 3-hydroxy oxindoles through a decarboxylative aldol addition of trifluoromethyl α-fluorinatedgem-diols to N-benzyl isatins, Angew. Chem. Int. Ed. 52 (2013) 5566-5570.

    26. [26]

      [26] P. Zhang, C. Wolf, Synthesis of pentafluorinated β-hydroxy ketones, J. Org. Chem. 79 (2012) 8840-8844.

    27. [27]

      [27] J.P. John, D.A. Colby, Synthesis of α-halo-α,α-difluoromethyl ketones by a trifluoroacetate release/halogenation protocol, J. Org. Chem. 78 (2011) 9163-9168.

    28. [28]

      [28] Z.M. Qiu, D.J. Burton, A general route to a,a-difluoroketones, Tetrahedron Lett. 34 (1993) 3239-3242.

    29. [29]

      [29] K.C. Kwak, H. Oh, Y.G. Yun, et al., Addition of a,a-difluoroiodomethylcyclohexyl ketone to alkenes under copper catalyst, Bull. Korean Chem. 23 (2002) 157-159.

    30. [30]

      [30] Z.M. Qiu, D.J. Burton, Synthesis of γ-(electron-withdrawing group)-substituted aa-difluoro ketones by UV-initiated addition of iododifluoromethyl ketones with electron-deficient alkenes, J. Org. Chem. 60 (1995) 6798-6805.

  • 加载中
    1. [1]

      Liliang ChuXiaoyan ZhangJianing LiXuelei DengMiao WuYa ChengWeiping ZhuXuhong QianYunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896

Metrics
  • PDF Downloads(0)
  • Abstract views(684)
  • HTML views(16)

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