研究论文

在含水介质中铜催化交叉氧化偶联反应合成β-酰基-α-氨基酸衍生物

  • 周安西 ,
  • 周晓菲 ,
  • 毛刘量 ,
  • 郑大贵 ,
  • 祝显虹 ,
  • 陈宗保
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  • a 上饶师范学院 江西省普通高校应用有机化学重点实验室 上饶 334001;
    b 江西科技师范大学有机功能分子研究所 江西省有机功能分子重点实验室 南昌 330013

收稿日期: 2018-09-06

  修回日期: 2018-12-10

  网络出版日期: 2018-12-21

基金资助

江西省教育厅科学技术研究(No.GJJ161059)、江西省重点研发计划(No.20161BBF60042)和上饶师范学院大学生学术科技研究(No.XS201723)资助项目.

Copper-Catalyzed Oxidative Cross-Coupling Reactions for the Synthesis of β-Acyl-α-amino Acid Derivatives in Aqueous Medium

  • Zhou Anxi ,
  • Zhou Xiaofei ,
  • Mao Liuliang ,
  • Zheng Dagui ,
  • Zhu Xianhong ,
  • Chen Zongbao
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  • a Key Laboratory of Applied Organic Chemistry, Higher Institutions of Jiangxi Province, Shangrao Normal University, Shangrao 334001;
    b Key Laboratory of Organic Chemistry in Jiangxi Province, Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013

Received date: 2018-09-06

  Revised date: 2018-12-10

  Online published: 2018-12-21

Supported by

Project supported by the Science and Technology Research Projects of the Education Department of Jiangxi Province (No.GJJ161059),the Key R&D Project of Jiangxi Province (No.20161BBF60042) and the Academic Research Project for College Students of Shangrao Normal University (No.XS201723).

摘要

报道了一种铜催化N-芳基甘氨酸酯与烯醇硅醚交叉氧化偶联反应合成β-酰基-α-氨基酸酯的新方法.该反应的特点在于:反应产率较高,反应条件温和(如室温环境和廉价的催化剂等),以及可以在含水介质中顺利进行.

本文引用格式

周安西 , 周晓菲 , 毛刘量 , 郑大贵 , 祝显虹 , 陈宗保 . 在含水介质中铜催化交叉氧化偶联反应合成β-酰基-α-氨基酸衍生物[J]. 有机化学, 2019 , 39(4) : 1070 -1078 . DOI: 10.6023/cjoc201809011

Abstract

A novel copper-catalyzed oxidative cross-coupling reaction between N-arylglycine esters and Silyl enol ethers for the synthesis of β-acyl-α-amino acid esters has been developed. The features of this reaction are high reaction yields, mild reaction conditions (such as room temperature environments and inexpensive catalysts, etc.) and smooth operation in aqueous medium.

参考文献

[1] Hunt, S. In Chemistry and Biochemistry of the Amino Acids, Ed.:Barrett, G. C., Chapman and Hall, London, 1985, p. 55.
[2] Williams, R. M.; Burnett, C. M. New Tricks in Amino Acid Synthsis:Applications to Complex Natural Products, ACS, Washington, DC, 2009, p. 420.
[3] Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889.
[4] Andrew, B. H. Amino Acids, Peptides and Proteins in Organic Chemistry, Wiley-VCH, Weinheim, Germany, 2011.
[5] Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995.
[6] Andrew, B. H. Amino Acids, Peptides and Proteins in Organic Chemistry, Vol. 3, Wiley-VCH, Weinheim, Germany, 2011.
[7] Strecker, A. Ann. Chem. Pharm. 1850, 75, 27.
[8] Ugi, I. Angew. Chem., Int. Ed. 1962, 1, 8.
[9] Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445.
[10] Xie, Z.; Liu, X.; Liu, L. Org. Lett. 2016, 18, 2982.
[11] Zhao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 7075.
[12] Zhu, S.; Rueping, M. Chem. Commun. 2012, 48, 11960.
[13] Huo, C.; Wang, C.; Sun, C.; Jia, X.; Wang, X.; Chang, W.; Wu, M. Adv. Synth. Catal. 2013, 355, 1911.
[14] Huo, C.; Wang, C.; Wu, M.; Jia, X.; Xie, H.; Yuan, Y. Adv. Synth. Catal. 2014, 356, 411.
[15] Li, K.; Tan, G.; Huang, J.; Song, F.; You, J. Angew. Chem., Int. Ed. 2013, 52, 12942.
[16] Ramana, D. V.; Chowhan, L. R.; Chandrasekharam, M. ChemistrySelect 2017, 2, 2241.
[17] Salman, M.; Zhu, Z.-Q.; Huang, Z.-Z. Org. Lett. 2016, 18, 1526.
[18] Wei, X.-H.; Wang, G.-W.; Yang, S.-D. Chem. Commun. 2015, 51, 832.
[19] Li, Y.-J.; Li, X.; Zhang, S.-X.; Zhang, Zhao, Y.-L.; Liu, Q. Chem. Commun. 2015, 51, 11564.
[20] Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.
[21] Davies, H. M. L.; Venkataramani, C.; Hansen, T.; Hopper, D. W. J. Am. Chem. Soc. 2003, 125, 6462.
[22] Davies, H. M. L.; Venkataramani, C. Angew. Chem., Int. Ed. 2002, 41, 2197.
[23] Davies, H. M. L.; Jin, Q. Org. Lett. 2004, 6, 1769.
[24] Davies, H. M. L.; Venkataramani, C. Org. Lett. 2001, 3, 1773.
[25] Axten, J. M.; Ivy, R.; Krim, L.; Winkler, J. D. J. Am. Chem. Soc. 1999, 121, 6511.
[26] Xiao, T.; Li, L.; Lin, G.; Mao, Z.-W.; Zhou, L. Org. Lett. 2014, 16, 4232.
[27] Qiu, L.; Guo, X.; Qian, Y.; Jing, C.; Ma, C.; Liu, S.; Hu, W. Chem. Commun. 2016, 52, 11831.
[28] Yu, H.; Xu, Y.; Dong, R.; Fang, Y. Adv. Synth. Catal. 2017, 359, 39.
[29] Wei, X.-H.; Zhao, L.-B.; Zhou, H.-C. RSC Adv. 2017, 7, 16561.
[30] Yu, H.; Shen, J. Org. Lett. 2014, 16, 3204.
[31] Zhu, Z.-Q.; Bai, P.; Huang, Z.-Z. Org. Lett. 2014, 16, 4881.
[32] Peng, H.; Yu, J.-T.; Jiang, Y.; Yang, H.; Cheng, J. J. Org. Chem. 2014, 79, 9847.
[33] Zhu, Z.-Q.; Xie, Z.-B.; Le, Z.-G. Synlett 2017, 28, 485.
[34] Segundo, M. S.; Guerrero, I.; Correa, A. Org. Lett. 2017, 19, 5288.
[35] Wei, W.-T.; Song, R.-J.; Li, J.-H. Adv. Synth. Catal. 2014, 356, 1703.
[36] Jia, X.; Liu, X.; Shao, Y.; Yuan, Y.; Zhu, Y.; Hou, W.; Zhang, X. Adv. Synth. Catal. 2017, 359, 4399.
[37] Chen, T.-T.; Cai, C. Synlett 2017, 28, 1368.
[38] Zhao, L.; Baslé, O.; Li, C.-J. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 4106.
[39] Zhang, G.; Zhang, Y.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 10429.
[40] Gao, X.-W.; Meng, Q.-Y.; Xiang, M.; Chen, B.; Feng, K.; Tung, C.-H.; Wu, L.-Z. Adv. Synth. Catal. 2013, 355, 2158.
[41] Gao, X.-W.; Meng, Q.-Y.; Li, J.-X.; Zhong, J.-J.; Lei, T.; Li, X.-B.; Tung, C.-H.; Wu, L.-Z. ACS Catal. 2015, 5, 2391.
[42] Yoo, W.-J.; Tanoue, A.; Kobayashi, S. Asian J. Org. Chem. 2014, 3, 1066.
[43] Xie, J.; Huang, Z.-Z. Angew. Chem. Int. Ed. 2010, 49, 10181.
[44] Liu, P.; Wang, Z.; Lin, J.; Hu, X. Eur. J. Org. Chem. 2012, 1583.
[45] Dilman, A. D.; Ioffe, S. A. Chem. Rev. 2003, 103, 733.
[46] Gilman, H.; Clark, R. N. J. Am. Chem. Soc. 1947, 69, 967.
[47] Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503.
[48] Kobayashi, S.; Mukaiyama, T. Chem. Lett. 1989, 297.
[49] Kobayashi, S.; Uchiro, T.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247.
[50] Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707.
[51] Mukaiyama, T.; Kashiwagi, K.; Matsui, S. Chem. Lett. 1989, 1397.
[52] Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153.
[53] Narasaka, K.; Soai, K.; Mukaiyama, T. Chem. Lett. 1974, 1223.
[54] Narasaka, K.; Soai, K.; Aikawa, Y.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1976, 49, 779.
[55] Kitajima, H.; Katsuki, T. Synlett 1997, 568.
[56] Kobayashi, S.; Manabe, K.; Ishitani, H.; Matsuo, J.-I. Sci. Synth. 2002, 4, 317.
[57] Yang, B.; Yang, T.-T.; Li, X.-A.; Wang, J.-J.; Yang, S.-D. Org. Lett. 2013, 15, 5024.
[58] Ding, Y.-B.; Liu, Y.-C. Chin. J. Org. Chem. 1990, 10, 488(in Chinese).(丁岩冰, 刘有成. 有机化学, 1990, 10, 488.)
[59] Liu, Y.-C.; Ding, Y.-B.; Liu, Z.-L. Acta Chim. Sinica 1990, 48, 1199(in Chinese).(刘有成, 丁岩冰, 刘中立, 化学学报, 1990, 48, 1199.)
[60] Liu, Y.-C.; Liu, Z.-L.; Wu, L.-M.; Chen, P. Tetrahedron Lett. 1985, 26, 4201.
[61] Kobayashi, S.; Ishitani, H. J. Chem. Soc., Chem. Commun. 1995, 1379.
[62] Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474.
[63] Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450.
[64] Kang, Q.; Zhang, Y. Org. Biomol. Chem. 2011, 9, 6715.

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