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2021 , Vol. 41 >Issue 6: 2228 - 2248

DOI: https://doi.org/10.6023/cjoc202010039

综述与进展

有机催化不对称合成3,4-二氢吡喃-2-酮和3,4-二氢吡啶-2-酮衍生物研究进展

  • 底慧明 ,
  • 刘云婷 ,
  • 马艳榕 ,
  • 杨鑫悦 ,
  • 金辉 ,
  • 张立新
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  • 沈阳化工大学功能分子研究所 辽宁省绿色功能分子设计与开发重点实验室 沈阳市靶向农药重点实验室 沈阳 110142

收稿日期: 2020-10-28

  修回日期: 2020-11-18

  网络出版日期: 2021-02-22

基金资助

辽宁省教育厅科学研究(LQ2020025); 南宁市科学研究与技术开发计划(20201043)

收起

Recent Advances in Organocatalytic Asymmetric Synthesis of 3,4-Dihydropyran-2-ones and 3,4-Dihydropyridin-2-ones

  • Huiming Di ,
  • Yunting Liu ,
  • Yanrong Ma ,
  • Xinyue Yang ,
  • Hui Jin ,
  • Lixin Zhang
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  • Shenyang Key Laboratory of Targeted Pesticides, Liaoning Key Laboratory of Green Functional Molecular Design and Development, Institute of Functional Molecules, Shenyang University of Chemical Technology, Shenyang 110142
*Corresponding authors.E-mail: ;

Received date: 2020-10-28

  Revised date: 2020-11-18

  Online published: 2021-02-22

Supported by

Science and Technology Project of Liaoning Education Department(LQ2020025); Nanning Scientific Research and Technology Development Program(20201043)

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摘要

3,4-二氢吡喃-2-酮和3,4-二氢吡啶-2-酮结构广泛存在于多种天然产物和具有药理活性的分子中, 因此高效合成手性3,4-二氢吡喃-2酮和3,4-二氢吡啶-2酮受到越来越多药物化学和有机化学研究者的关注. 近年来有机小分子催化的不对称反应已成为构建手性杂环化合物的有效方法. 综述了自2003年至今有机小分子催化的不对称反应合成手性3,4-二氢吡喃酮和3,4-二氢吡啶酮衍生物的研究进展, 并根据不同的催化剂类型及反应机理进行分类讨论.

关键词： 有机催化; 不对称催化; 3,4-二氢吡喃酮; 3,4-二氢吡啶酮

本文引用格式

底慧明 , 刘云婷 , 马艳榕 , 杨鑫悦 , 金辉 , 张立新 . 有机催化不对称合成3,4-二氢吡喃-2-酮和3,4-二氢吡啶-2-酮衍生物研究进展[J]. 有机化学, 2021 , 41(6) : 2228 -2248 . DOI: 10.6023/cjoc202010039

Abstract

3,4-Dihydropyranone and 3,4-dihydropyridinone substructures are widely found in a variety of natural products and pharmacologically active molecules, so the efficient synthesis of chiral 3,4-dihydropyranones and 3,4-dihydropyridinones has received more and more attention from pharmaceutical chemists and organic chemists. In recent years, organocatalytic asymmetric reaction has become an efficient synthetic method for the construction of chiral heterocyclic compounds. In this review, the remarkable progress and advances in organocatalytic asymmetric reactions for the synthesis of 3,4-dihydro- pyranones and 3,4-dihydropyridinones from 2003 to 2020 are summarized and discussed based on the different types of organocatalysts and reaction mechanisms.

Key words： organocatalysis; asymmetric catalysis; 3,4-dihydropyranones; 3,4-dihydropyridinones

参考文献

[1]
(a) Halliwell, B. Biochem. J. 2007, 401,1.
[1]
(b) Robert, S.; Bertolla, C.; Masereel, B.; Dogné, J.-M.; Pochet, L. J. Med. Chem. 2008, 51,3077.
[1]
(c) Yang, J.; Liu, G.-Y.; Dai, F.; Cao, X.-Y.; Kang, Y.; Hu, L.-M.; Jin, X.-L. Bioorg. Med. Chem. Lett. 2011, 21,6420.
[1]
(d) Nantermet, P. G.; Barrow, J. C.; Selnick, H. G.; Homnick, C. F.; Freidinger, R. M.; Chang, R. S. L.; O’Malley, S. S.; Reiss, D. R.; Broten, T. P.; Ransom, R. W.; Pettibone, D. J.; Olah, T.; Forray, C. Bioorg. Med. Chem. Lett. 2000, 10,1625.
[1]
(e) Goodman, K. B.; Cui, H.; Dowdell, S. E.; Gaitanopoulos, D. E.; Ivy, R. L.; Sehon, C. A.; Stavenger, R. A.; Wang, G. Z.; Viet, A. Q.; Xu, W.; Ye, G.; Semus, S. F.; Evans, C.; Fries, H. E.; Jolivette, L. J.; Kirkpatrick, R. B.; Dul, E.; Khandekar, S. S.; Yi, T.; Jung, D. K.; Wright, L. L.; Smith, G. K.; Behm, D. J.; Bentley, R.; Doe, C. P.; Hu, E.; Lee, D. J. Med. Chem. 2007, 50,6.
[2]
(a) Ying, A.; Wu, C.; Fu, Y.; Ren, S.; Liang, H. Chin. J. Org. Chem. 2012, 32,1587(in Chinese).
[2]
( 应安国, 武承林, 付永前, 任世斌, 梁华定, 有机化学, 2012, 32,1587.)
[2]
(b) Xiang, S.-H.; Tan, B. Nat. Commun. 2020, 11,3786.
[2]
(c) Lassaletta, J. M. Nat. Commun. 2020, 11,3787.
[2]
(d) Zhang, M.-M.; Luo, Y.-Y.; Lu, L.-Q.; Xiao, W.-J. Acta Chim. Sinica 2018, 76,838(in Chinese).
[2]
( 张毛毛, 骆元元, 陆良秋, 肖文精, 化学学报, 2018, 76,838.)
[3]
(a) Dalko, P. I. Comprehensive Enantioselective Organocata-lysis: Catalysts, Reactions, and Applications, Wiley, New York, 2013.
[3]
(b) Chen, X.-K.; Wang, H.-L.; Jin, Z.-C.; Chi, Y. R. Chin. J. Chem. 2020, 38,1167.
[4]
(a) Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2,167.
[4]
(b) Chanda, T.; Zhao, J. C. -G. Adv. Synth. Catal. 2018, 360,2.
[4]
(c) Lin, Y. ; D., D-M. Chin. J. Org. Chem. 2020, 40,3214(in Chinese).
[4]
( 林晔, 杜大明, 有机化学, 2020, 40,3214.)
[4]
(d) Sun, L.-H.; Liang, Z.-Q.; Ye, S. Acta Chim. Sinica 2014, 72,841(in Chinese).
[4]
( 孙利辉, 梁志钦, 叶松, 化学学报, 2014, 72,841.)
[4]
(e) Zheng, Y.; Xie, Z.-Z.; Chen, K.; Xiang, H.-Y.; Yang, H. Chin. J. Org. Chem. 2021, 41,1(in Chinese).
[4]
( 郑雨, 谢珍珍, 陈凯, 向皞月, 阳华, 有机化学, 2021, 41,1.)
[5]
Belmessieri, D.; Morrill, L. C.; Simal, C.; Slawin, A. M.; Smith, A. D. J. Am. Chem. Soc. 2011, 133,2714.
[6]
(a) Oehlrich, D.; Berthelot, D. J. -C.; Gijsen, H. J. M. J. Med. Chem. 2011, 54,699.
[6]
(b) Chen, J.; Lu, M.-M.; Liu, B.; Chen, Z.; Li, Q.-B.; Tao, L.-J.; Hu, G.-Y. Bioorg. Med. Chem. Lett. 2012, 22,2300.
[6]
(c) Li, P.; Liu, L.-J.; Liu, J.-T. Org. Biomol. Chem. 2011, 9,74.
[6]
(d) Yi, H.; Song, L. P.; Wang, W.; Liu, J. N.; Zhu, S. Z.; Deng, H. M.; Shao, M. Chem. Commun. 2010, 46,6941.
[7]
Morrill, L. C.; Douglas, J.; Lebl, T.; Slawin, A. M.; Fox, D. J.; Smith, A. D. Chem. Sci. 2013, 4,4146.
[8]
Simal, C.; Lebl, T.; Slawin, A. M. Z.; Smith, A. D. Angew. Chem., Int. Ed. 2012, 51,3653.
[9]
Yeh, P. P.; Daniels, D. S. B.; Fallan, C.; Gould, E.; Simal, C.; Taylor, J. E.; Smith, A. D. Org. Biomol. Chem. 2015, 13,2177.
[10]
Stark, D. G.; Young, C. M.; O’Riordan, T. J. C.; Slawin, A. M. Z.; Smith, A. D. Org. Biomol. Chem. 2016, 14,8068.
[11]
Stark, D. G.; Morrill, L. C.; Cordes, D. B.; Slawin, A. M. Z.; O’Riordan, T. J. C.; Smith, A. D. Chem. Asian J. 2016, 11,395.
[12]
Young, C. M.; Stark, D. G.; West, T. H.; Taylor, J. E.; Smith, A. D. Angew. Chem., Int. Ed. 2016, 55,14394.
[13]
Lee, J. W.; Mayer-Gall, T.; Opwis, K.; Song, C. E.; Gutmann, J. S.; List, B. Science 2013, 341,1225.
[14]
Wang, S.; Izquierdo, J.; Rodríguez-Escrich, C.; Pericàs, M. A. ACS Catal. 2017, 7,2780.
[15]
Zhang, Y.-C.; Geng, R.-L.; Song, J.; Gong, L.-Z. Org. Lett. 2020, 22,2261.
[16]
Liu, H.; Slawin, A. M. Z.; Smith, A. D. Org. Lett. 2020, 22,1301.
[17]
(a) Nozawa, K.; Nakajima, S. J. Nat. Prod. 1979, 42,374.
[17]
(b) Koizumi, Y.; Arai, M.; Tomoda, H.; Omura, S. Biochim. Biophys. Acta, Mol. Cell Res. 2004,1693 , 47.
[17]
(c) He, R.; Ding, C.; Maruoka, K. Angew. Chem., Int. Ed. 2009, 48,4559.
[17]
(d) Guo, C.; Song, J.; Luo, S.-W.; Gong, L.-Z. Angew. Chem., Int. Ed. 2010, 49,5558.
[17]
(e) Yao, J.; Wei, X.; Lu, Y. Biochem. Biophys. Res. Commun. 2016, 473,867.
[18]
(a) Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T. Chem. Rev. 2015, 115,9307.
[18]
(b) Chen, X. -.; Gao, Z. -.; Ye, S. Acc. Chem. Res. 2020, 53,690.
[18]
(c) Wang, A.; Xiao, Y. -.; Zhou, Y.; Xu, J. -.; Liu, H. Chin. J. Org. Chem. 2017, 37,2590(in Chinese).
[18]
( 王翱, 肖永龙, 周宇, 徐进宜, 柳红, 有机化学, 2017, 37,2590.)
[19]
He, M.; Uc, G. J.; Bode, J. W. J. Am. Chem. Soc. 2006, 128,15088.
[20]
Wang, D.-L.; Liang, Z.-Q.; Chen, K.-Q.; Sun, D.-Q.; Ye, S. J. Org. Chem. 2015, 80,5900.
[21]
Davies, A. T.; Pickett, P. M.; Slawin, A. M. Z.; Smith, A. D. ACS Catal. 2014, 4,2696.
[22]
(a) Ulmschneider, S.; Muller-Vieira, U.; Klein, C. D.; Antes, I.; Lengauer, T.; Hartmann, R. W. J. Med. Chem. 2005, 48,1563.
[22]
(b) Hudson, S.; Kiankarimi, M.; Eccles, W.; Mostofi, Y. S.; Genicot, M. J.; Dwight, W.; Fleck, B. A.; Gogas, K.; Wade, W. S. Bioorg. Med. Chem. Lett. 2008, 18,4495.
[22]
(c) Camps, P.; Formosa, X.; Galdeano, C.; Gomez, T.; Munoz-Tor- rero, D.; Scarpellini, M.; Viayna, E.; Badia, A.; Clos, M. V.; Camins, A.; Pallas, M.; Bartolini, M.; Mancini, F.; Andrisano, V.; Estelrich, J.; Lizondo, M.; Bidon-Chanal, A.; Luque, F. J. J. Med. Chem. 2008, 51,3588.
[23]
Biswas, A.; Sarkar, S. D.; Fröhlich, R.; Studer, A. Org. Lett. 2011, 13,4966.
[24]
Mukherjee, S.; Ghosh, A.; Marelli, U. K.; Biju, A. T. Org. Lett. 2018, 20,2952.
[25]
Hao, L.; Chen, S.; Xu, J.; Tiwari, B.; Fu, Z., Li, T.; Chi, Y. R. Org. Lett. 2013, 15,4956.
[26]
Gharpure, S. J.; Vishwakarma, D. S. Eur. J. Org. Chem. 2020,6887.
[27]
Lee, A.; Younai, A.; Price, C. K.; Izquierdo, J.; Mishra, R. K.; Scheidt, K. A. J. Am. Chem. Soc. 2014, 136,10589.
[28]
(a) Lv, H.; Zhang, Y.-R.; Huang, X.-L.; Ye, S. Adv. Synth. Catal. 2008, 350,2715.
[28]
(b) Huang, X.-L.; He, L.; Shao, P.-L.; Ye, S. Angew. Chem., Int. Ed. 2009, 48,192.
[28]
(c) Shao, P.-L.; Chen, X.-Y.; Ye, S. Angew. Chem., Int. Ed. 2010, 49,8412.
[28]
(d) Shao, P.-L.; Chen, X.-Y.; Sun, L.-H.; Ye, S. Tetrahedron Lett. 2010, 51,2316.
[28]
(e) Zhang, H.-M.; Gao, Z.-H.; Ye, S. Org. Lett. 2014, 16,3079.
[29]
Lv, H.; Chen, X.-Y.; Sun, L.; Ye, S. J. Org. Chem. 2010, 75,6973.
[30]
Jian, T.-Y.; Chen, X.-Y.; Sun, L.-H.; Ye, S. Org. Biomol. Chem. 2013, 11,158.
[31]
Wang, C.-Y.; Wang, Z.-Y.; Yang, J.; Shi, S.-H.; Hui, X.-P. Org. Lett. 2020, 22,4440.
[32]
(a) Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. J. Am. Chem. Soc. 2010, 132,8810.
[32]
(b) Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2009, 131,14176.
[33]
(a) De, Sarkar, S.; Studer, A. Angew. Chem., Int. Ed. 2010, 49,9266.
[33]
(b) Rong, Z.-Q.; Jia, M.-Q.; You, S.-L. Org. Lett. 2011, 13,4080.
[34]
Kravina, A. G.; Mahatthananchai, J.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51,9433.
[35]
(a) Ball-Jones, N. R.; Badillo, J. J.; Franz, A. K. Org. Biomol. Chem. 2012, 10,5165.
[35]
(b) Cheng, D.; Ishihara, Y.; Tan, B.; Barbas, III, C. F. ACS. Catal. 2014, 4,743.
[35]
(c) Pavlovska, T. L.; Redkin, R. G.; Lipson, V. V.; Atamanuk, D. V. Mol. Diversity 2016, 20,299.
[35]
(d) Yu, B.; Cai, Z.; Wang, S.; Liu, H. Chin. J. Org. Chem. 2017, 37,1952(in Chinese).
[35]
( 余斌, 蔡祖恽, 王帅, 刘宏民, 有机化学, 2017, 37,1952.)
[36]
Xie, D.; Yang, L.; Lin, Y.; Zhang, Z.; Chen, D.; Zeng, X.; Zhong, G. Org. Lett. 2015, 17,2318.
[37]
Zhao, L.-L.; Li, X.-S., Cao, L.-L.; Zhang, R.; Shi, X.-Q.; Qi, J. Chem. Commun. 2017, 53,5985.
[38]
Piera, J.; Bäckvall, J.-E. Angew. Chem., Int. Ed. 2008, 47,3506.
[39]
Xie, D.; Shen, D.; Chen, Q.; Zhou, J.; Zeng, X.; Zhong, G. J. Org. Chem. 2016, 81,6136.
[40]
Axelsson, A.; Hammarvid, E.; Ta, L.; Sundén, H. Chem. Commun. 2016, 52,11571.
[41]
Sun, F.-G.; Sun, L.-H.; Ye, S. Adv. Synth. Catal. 2011, 353,3134.
[42]
Zhang, H.; Jia, W.; Liang, Z.; Ye, S. Asian J. Org. Chem. 2014, 3,462.
[43]
Gao, Z.-H.; Chen, X.-Y.; Zhang, H.-M.; Ye, S. Chem. Commun. 2015, 51,12040.
[44]
Chen, K.; Gao, Z.; Ye, S. Angew. Chem., Int. Ed. 2019, 58,1183.
[45]
Yan, J.; Song, Z.; Zhao, C.; Shi, K.; Yang, L.; Zhong, G. Org. Lett. 2020, 22,3329.
[46]
Cheng, J.; Huang, Z.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52,8592.
[47]
Zhang, Z.; Zeng, X.; Xie, D.; Chen, D.; Ding, L.; Wang, A.; Zhong, G. Org. Lett. 2015, 17,5052.
[48]
Chen, X.-Y.; Gao, Z.-H.; Song, C.-Y.; Zhang, C.-L.; Wang, Z.-X.; Ye, S. Angew. Chem., Int. Ed. 2014, 53,11611.
[49]
Que, Y.; Lu, Y.; Wang, W.; Wang, Y.; Wang, H.; Yu, C.; Yao, C. Chem. Asian J. 2016, 11,678.
[50]
(a) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125,12672.
[50]
(b) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127,119.
[50]
(c) Connon, S. J. Chem Commun. 2008, 22,2499.
[51]
Zhang, M. L.; Wu, Z. J.; Zhao, J. Q.; Luo, Y.; Xu, X. Y.; Zhang, X. M.; Yuan, W. C. Org. Lett. 2016, 18,5110.
[52]
(a) Burke, H. M.; McSweeney, L.; Scanlan, E. M. Nat. Commun. 2017, 8,15655.
[52]
(b) Bahlinger, A.; Fritz, S. P.; Wennemers, H. Angew. Chem., Int. Ed. 2014, 53,8779.
[52]
(c) Schäberle, T. F. Beilstein J. Org. Chem. 2016, 12,571.
[53]
Jin, H.; Lee, J.; Shi, H.; Lee, J. Y.; Yoo, E. J.; Song, C. E.; Ryu, D. H. Org. Lett. 2018, 20,1584.
[54]
Cui, L. Y.; Lv, D.; Wang, Y. M.; Fan, Z. J.; Li, Z. M.; Zhou, Z. H. J. Org. Chem. 2018, 83,4221.
[55]
Zhang, S.; Lv, M.; Yin, S.; Li, N.; Zhang, J.; Wang, X. Adv. Synth. Catal. 2016, 358,143.
[56]
Zhang, Z.-P.; Chen, L.; Li, X.; Cheng, J.-P. J. Org. Chem. 2018, 83,2714.
[57]
Xian, J.; Chen, L.; Ye, L.; Sun, Y.; Shi, Z.; Zhao, Z.; Li, X. Tetrahedron 2019, 75,2350.
[58]
Chen, L.; Zhang, X.; Shi, K.-J.; Leng, H.-J.; Li, Q.-Z.; Liu, Y.; Li, J.-L. J. Org. Chem. 2020, 85,9454.
[59]
(a) GrAger, H.; Wilken, J. Angew. Chem., Int. Ed. 2001, 40,529.
[59]
(b) List, B. Tetrahedron 2002, 58,5573.
[59]
(c) Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44,794.
[59]
(d) Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44,4212.
[59]
(e) Zhao, C.; Feng, Z.; Xu, G.; Gao, A.; Chen, J.; Wang, Z.; Xu, P. Angew. Chem., Int. Ed. 2020, 59,3058.
[60]
Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42,1498.
[61]
Wang, J.; Yu, F.; Zhang, X.; Ma, D. Org. Lett. 2008. 10,2561.
[62]
Sinha, D.; Perera, S.; Zhao, J. C. G. Chem.-Eur. J. 2013, 19,6976.
[63]
Kano, T.; Maruyama, H.; Homma, C.; Maruoka, K. Chem. Commun. 2018, 54,3496.
[64]
Kelley, A. M.; Haywood, R. D.; White, J. C.; Petersen, K. S. ChemistrySelect 2020, 5,3018.
[65]
Shirakawa, S.; Maruoka, K. Angew. Chem. Int. Ed. 2013, 52,4312.
[66]
Destro, D.; Bottinelli, C.; Ferrari, L.; Albanese, D. C. M.; Bencivenni, G.; Gillick-Healy, M. W.; Adamo, M. F. A. J. Org. Chem. 2020, 85,5183.
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