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2019 , Vol. 39 >Issue 9: 2345 - 2364

DOI: https://doi.org/10.6023/cjoc201903006

综述与进展

甘氨酸衍生物α-C(sp3)-H键官能团化反应的研究进展

  • 祝志强 ,
  • 肖利金 ,
  • 谢宗波 ,
  • 乐长高
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  • 东华理工大学化学生物与材料科学学院 核资源与环境国家重点实验室 南昌 330013

收稿日期: 2019-03-03

  修回日期: 2019-04-15

  网络出版日期: 2019-04-26

基金资助

国家自然科学基金（Nos.21602027，11765002）、江西省教育厅科学技术（No.GJJ170458）和中国博士后基金（No.2018M632595）资助项目.

收起

Recent Advances in the α-C(sp3)-H Bond Functionalization of Glycine Derivatives

  • Zhu Zhiqiang ,
  • Xiao Lijin ,
  • Xie Zongbo ,
  • Le Zhanggao
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  • State Key Laboratory of Nuclear Resources and Environment, School of Chemistry, Biology and Material Science, East China University of Technology, Nanchang 330013

Received date: 2019-03-03

  Revised date: 2019-04-15

  Online published: 2019-04-26

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21602027, 11765002), the Foundation of Jiangxi Educational Committee (No. GJJ170458) and the China Postdoctoral Science Foundation (No. 2018M632595).

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摘要

α-氨基酸是构成蛋白质的基本结构单元，不仅广泛存在于许多具有重要生物活性的有机分子和天然产物中，而且还可作为有机催化剂或配体用于不对称合成.其中，甘氨酸类化合物在有机合成中是一类非常有用的模块，通过甘氨酸衍生物的α-C（sp3）-H键官能团化高效构建种类丰富的α-取代的α-氨基酸是一种极吸引人的合成策略.介绍了近年来甘氨酸衍生物α-C（sp3）-H活化后与不同有机试剂偶联构建碳-碳键和碳-杂键以及甘氨酸衍生物参与的氧化串联/环化反应的研究进展.

关键词： 甘氨酸; 碳-氢键; 官能团化; 脱氢交叉偶联; 串联环化

本文引用格式

祝志强 , 肖利金 , 谢宗波 , 乐长高 . 甘氨酸衍生物α-C(sp3)-H键官能团化反应的研究进展[J]. 有机化学, 2019 , 39(9) : 2345 -2364 . DOI: 10.6023/cjoc201903006

Abstract

α-Amino acids are the units of proteins, which not only widely occur in many biological important compounds and natural products, but also are useful as organic catalysts or ligands for asymmetric synthesis. Among them, glycines are particularly useful building blocks in organic synthesis. Direct C(sp3)-H bond functionalization of glycine derivatives provided an attractive synthesis strategy for the construction of a variety of α-substituted α-amino acids. The recent progress in the α-C(sp3)-H bond activation of glycine derivatives, with various reagents to form carbon-carbon and carbon-heteroatom bond, and oxidative coupling/cyclization reaction involving glycine derivatives is reviewed.

Key words： glycines; C-H bond; functionalization; cross-dehydrogenative-coupling; cascade cyclization

参考文献

[1] (a) Pollegioni, L.; Servi, S. Non-natural Amino Acids:Methods and Protocols, Springer, New York, 2012.
(b) Hughes, A. B. Amino Acids, Peptides and Proteins in Organic Chemistry, Wiley VCH, Weinheim, 2011.
[2] (a) Soloshonok, V. A.; Izawa, K. Asymmetric Synthesis and Application of α-Amino Acids, American Chemical Society, Washington DC, 2009, Vol. 1009.
(b) He, G.; Wang, B.; Nack, W. A.; Chen, G. Acc. Chem. Res. 2016, 49, 635.
(c) Bhat, S. V.; Nagasampagi, B. A.; Sivakumar, M. Chemistry of Natural Products, Springer, Berlin, 2005, p. 317.
(d) Li, X.; Xiong, W.; Ding, Q. Chin. J. Org. Chem. 2019, 39, 1874(in Chinese). (李小芳, 熊伟康, 丁秋平, 有机化学, 2019, 39, 1874.)
[3] (a) Albericio, F.; Kruger, H. G. Future Med. Chem. 2012, 4, 1527.
(b) Craik, D. J.; Fairlie, D. P.; Liras, S.; Price, D. Chem. Biol. Drug Des. 2013, 81, 136.
(c) Kaspar, A. A.; Reichert, J. M. Drug Discovery Today 2013, 18, 807.
[4] (a) Noisier, A. F. M.; Brimble, M. A. Chem. Rev. 2014, 114, 8775.
(b) Metz, A. M.; Kozlowski, M. C. J. Org. Chem. 2015, 80, 1.
[5] (a) Bauer, M.; Wang, W.; Lorion, M. M.; Dong, C.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 203.
(b) Stepan, A. F.; White, M. C. Nature 2016, 537, 214.
(c) Uhlig, T.; Kyprianou, T.; Martinelli, F. G.; Oppici, C. A.; Heiligers, D.; Heiligers, D.; Hills, X. R.; Calvo, P. V. Eup. Open Proteomics 2014, 4, 58.
(d) Xiao, H.; Chatterjee, A.; Choi, S. H.; Bajjuri, K. M.; Sinha, S. C.; Schultz, P. G. Angew. Chem., Int. Ed. 2013, 52, 14080.
[6] (a) Strecker, A. Ann. Chem. Pharm. 1850, 75, 27.
(b) Ugi, I. Angew. Chem., Int. Ed. 1962, 1, 8.
(c) Petasis, N. A.; Zavialov, A. I. J. Am. Chem. Soc. 1997, 119, 445.
[7] (a) Bayer, A.; Kazmaier, U. J. Org. Chem. 2014, 79, 8491.
(b) Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013.
[8] (a) Brown, Jihn. M.; Cooley, Nei. A. Chem. Rev. 1988, 88, 1031.
(b) Godula, K.; Sames, D. Science 2006, 312, 67.
(c) Bergman, R. G. Nature 2007, 446, 391.
[9] (a) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
(b) Sun, C.; L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293.
(c) Davies, H. M. L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857.
(d) Zhang, J.; Lu, Q. Q.; Liu, C.; Lei, A. W. Chin. J. Org. Chem. 2015, 35, 743(in Chinese). (张剑, 陆庆全, 刘超, 雷爱文, 有机化学, 2015, 35, 743.)
(e) Pei, P. K.; Zhang, F.; Yi, H.; Lei, A. W. Acta Chim. Sinica 2017, 75, 15(in Chinese). (裴朋昆, 张凡, 易红, 雷爱文, 化学学报, 2017, 75, 15.)
[10] (a) Engle, K. M.; Mei, T. S.; Wasa, M.; Yu, J. Q. Acc. Chem. Res. 2012, 45, 788.
(b) Roizen, J. L.; Harvey, M. E.; Du Bois, J. Acc. Chem. Res. 2012, 45, 911.
(c) Yang, L.; Huang, H. Chem. Rev. 2015, 115, 3468.
(d) Dong, Z.; Ren, Z.; Thompson, S. J.; Xu, Y.; Dong, G. Chem. Rev. 2017, 117, 9333.
(e) Liu, W.; Zheng, X, Y.; Zeng, J. G.; Cheng, P. Chin. J. Org. Chem. 2017, 37, 1(in Chinese). (刘薇, 郑昕宇, 曾建国, 程辟, 有机化学, 2017, 37, 1.)
[11] (a) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 3672.
(b) Li, C. J. Acc. Chem. Res. 2009, 42, 335.
[12] (a) Zhu, Z. Q.; Bai, P.; Huang, Z. Z. Org. Lett. 2014, 16, 4881.
(b) Salman, M.; Zhu, Z. Q.; Huang, Z. Z. Org. Lett. 2016, 18, 1526.
(c) Zhu, Z. Q.; Xie, Z. B.; Le, Z. G. J. Org. Chem. 2016, 81, 9449.
(d) Zhu, Z. Q.; Xie, Z. B.; Le, Z. G. Synlett. 2017, 28, 485.
(e) Zhu, Z. Q.; Xiao L. J.; Chen, Y.; Zhu, H. B.; Xie, Z. B.; Le, Z. G. Synthesis 2018, 50, 2775.
(f) Xiao L. J.; Zhu, Z. Q.; Guo, D.; Xie, Z. B.; Lu, Y.; Le, Z. G. Synlett 2018, 29, 1659.
(g) Zhu, Z. Q.; Xiao L. J.; Zhou, C. C.; Song, H. L.; Xie, Z. B.; Le, Z. G. Tetrahedron Lett. 2018, 59, 3326.
(h) Zhu, Z. Q.; Xiao L. J.; Guo, D.; Chen, X.; Ji, J. J.; Zhu, X.; Xie, Z. B.; Le, Z. G. J. Org. Chem. 2019, 84, 435.
[13] (a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1960, 82, 2640.
(b) Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170.
(c) Prier, C. K.; Rankic, D. A.; Mac Millan, D. W. C. Chem. Rev. 2013, 113, 5322.
[14] Luo, Y. R. Handbook of Bond Dissociation Energy in Organic Compound, CRC Press, Boca Raton, 2002.
[15] (a) Li, Z.; Bohle, D. S.; Li, C. J. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 8928.
(b) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2006, 128, 56.
[16] Zhao, L.; Li, C. J. Angew. Chem., Int. Ed. 2008, 47, 7075.
[17] Luo, M. H.; Jiang, Y. Y.; Xu, K.; Liu, Y. G.; Sun, B. G.; Zeng, C. C. Beilstein J. Org. Chem. 2018, 14, 499.
[18] Sud, A.; Sureshkumar, D.; Klussmann, M. Chem. Commun. 2009, 3169.
[19] Xie, J.; Huang, Z. Z. Angew. Chem., Int. Ed. 2010, 49, 10181.
[20] Liu, P.; Wang, Z.; Lin, J.; Hu, X. Eur. J. Org. Chem. 2012, 2012, 1583.
[21] Gao, X. W.; Meng, Q. Y.; Xiang, M.; Chen, B.; Feng, K.; Tung, C. H.; Wu, L. Z. Adv. Synth. Catal. 2013, 355, 2158.
[22] Zhang, G.; Zhang, Y.; Wang, R. Angew. Chem., Int. Ed. 2011, 50, 10429.
[23] Tan, Y. Q.; Yuan, W.; Gong, L.; Meggers, E. Angew. Chem., Int. Ed. 2015, 127, 13237.
[24] (a) Deng, G. J.; Zhao, L.; Li, C. J. Angew. Chem., Int. Ed. 2008, 47, 6278.
(b) Ochiai, M.; Miyamato, K.; Kaneaki, T.; Hayashi, S.; Nakanishi, W. Science 2011, 332, 448.
(c) Tran, B.; Li, B.; Driess, M.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 2555.
[25] Forkin, A. A.; Schreiner, P. R. Chem. Rev. 2002, 102, 1551.
[26] Wei, W. T.; Song, R. J.; Li, J. H. Adv. Synth. Catal. 2014, 356, 1703.
[27] Peng, H.; Yu, J. T.; Jiang, Y.; Yang, H.; Cheng, J. J. Org. Chem. 2014, 79, 9847.
[28] San Segundo, M.; Guerrero, I.; Correa, A. Org. Lett. 2017, 19, 5288.
[29] Mutra, M. R.; Dhandabani, G. K.; Wang, J. J. Adv. Synth. Catal. 2018, 360, 3960.
[30] Segundo, M. S.; Correa, A. ChemSusChem. 2018, 11, 3893.
[31] Li, K.; Tan, G.; Huang, J.; Song, F.; You, J. Angew. Chem., Int. Ed. 2013, 52, 12942.
[32] Li, K.; Wu, Q.; Lan, J.; You, J. S. Nat. Chem. 2015, 6, 8404.
[33] Tan, M.; Li, K.; Yin, J.; You, J. Chem. Commun. 2018, 54, 1221.
[34] (a) Inagaki, A.; Akita, M. Coord. Chem. Rev. 2010, 254, 1220.
(b) Narayanam, J. M.; Stephenson, C. R. Chem. Soc. Rev. 2011, 40, 102.
(c) Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687.
(d) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[35] (a) McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114.
(b) Petronijevic, F. R.; Nappi, M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2013, 135, 18323.
(c) Pirnot, M. T.; Rankic, D. A.; Martin, D. B.; MacMillan, D. W. C. Science 2013, 339, 1593.
[36] Xuan, J.; Zeng, T. T.; Feng, Z. J.; Deng, Q. H.; Chen, J. R.; Lu, L. Q.; Xiao, W. J.; Alper H. Angew. Chem., Int. Ed. 2015, 54, 1625.
[37] Ding, W.; Lu, L. Q.; Liu, J.; Liu, D.; Song, H. T.; Xiao W. J. J. Org. Chem. 2016, 81, 7237.
[38] Wang, C.; Guo, M. Z.; Qi, R. P.; Shang, Q. Y.; Liu, Q. Y.; Wang, S.; Zhao, L.; Wang, R.; Xu, Z. Q. Angew. Chem., Int. Ed. 2018, 130, 16067.
[39] (a) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 3672.
(b) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 6968.
(c) Li, Z.; Li, C. J. J. Am. Chem. Soc. 2004, 126, 11810.
[40] Xie, Z.; Liu, X.; Liu, L. Org. Lett. 2016, 18, 2982.
[41] (a) Muller, J.; Saunders, J. O. F.; Salituro, G.; Travins, J. M.; Yan, S.; Zhao, F.; Su, S. M. ACS Med. Chem. Lett. 2012, 3, 850.
(b) Zhang, L.; Wang, X.; Li, X.; Xu, W. J. Enzyme. Inhib. Med. Chem. 2014, 29, 333.
(c) Weigel, L. F.; Nitsche, C.; Graf, D.; Bartenschlager, R.; Klein, C. D. J. Med. Chem. 2015, 58, 7719.
[42] (a) Denis, J. N.; Correa, A.; Greene, A. E. J. Org. Chem. 1991, 56, 6939.
(b) Buyck, T.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2013, 52, 12714.
[43] (a) Shirakawa, S.; Maruoka, K. Angew. Chem., Int. Ed. 2013, 52, 4312.
(b) Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656.
[44] Zhao, L.; Baslé, O.; Li, C. J. Proc. Natl. Acd. Sci. U. S. A. 2009, 106, 4106.
[45] Zhu, S. Q.; Rueping, M. Chem. Commun. 2012, 48, 11960.
[46] Wang, Z. Q.; Hu, M.; Huang, X. C.; Gong, L. B.; Xie, Y. X.; Li, J. H. J. Org. Chem. 2012, 77, 8705.
[47] Huo, C.; Wang, C.; Wu, M.; Jia, X.; Xie, H.; Yuan, Y. Adv. Synth. Catal. 2014, 356, 411.
[48] Huo, C.; Yuan, Y.; Wu, M.; Jia, X.; Wang, X.; Chen, F.; Tang, J. Angew. Chem. 2014, 53, 13544.
[49] 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.
[50] Zhang, Y.; Ni, M. J.; Feng, B. N. Org. Biomol. Chem. 2016, 14, 1550.
[51] Wu, J. C.; Song, R. J.; Wang, Z. Q.; Huang, X. C.; Xie, Y. X.; Li, J. H. Angew. Chem., Int. Ed. 2012, 51, 3453.
[52] Huo, C.; Wang, C.; Sun, C.; Jia, X.; Wang, X.; Chang, W.; Wu, M. Adv. Synth. Catal. 2013, 355, 1911.
[53] Li, S. L.; Yang, X. R.; Wang, Y. W.; Zhou, H.; Zhang, B. Y.; Huang, G. X.; Zhang, Y.; Li Y. Adv. Synth. Catal. 2018, 360, 4452.
[54] Zhou, J. L.; Liu, J. C.; Chen, Q. Y. Chin. J. Org. Chem. 2009, 29, 1708(in Chinese). (周建良, 刘建超, 陈启元, 有机化学, 2009, 29, 1708.)
[55] Jin, C. A.; Xu, Q.; Feng, G. F.; Jin, Y.; Zhang, L. Y. Chin. J. Org. Chem. 2018, 38, 775(in Chinese). (金城安, 徐庆, 冯高峰, 金阳, 张连阳, 有机化学, 2018, 38, 775.)
[56] Jiao, J.; Zhang, J. R.; Liao, Y. Y.; Xu, L.; Hu, M.; Tang, R. Y. RSC Adv. 2017, 7, 30152.
[57] Ramana, D. V.; Chowhan, L. R.; Chandrasekharam, M. ChemistrySelect 2017, 2, 2241.
[58] Wei, Y. Y.; Wang, J.; Wang, Y. J.; Yao, X. Q.; Yang, C. X.; Huo, C. Org. Biomol. Chem. 2018, 16, 4985.
[59] Gao, Y. Z.; Tang, G.; Zhao, Y. F. Chin. J. Org. Chem. 2018, 38, 62(in Chinese). (高玉珍, 唐果, 赵玉芬, 有机化学, 2018, 38, 62.)
[60] Baslé, O.; Li, C. J. Chem. Commun. 2009, 4124.
[61] Yang, B.; Yang, T. T.; Li, X. A.; Wang, J. J.; Yang, S. D. Org. Lett. 2013, 15, 5024.
[62] Zhi, H.; Ung, S. P. M.; Liu, Y.; Zhao, L.; Li, C. J. Adv. Synth. Catal. 2016, 358, 2553.
[63] Jia, X.; Liu, X.; Shao, Y.; Yuan, Y.; Zhu, Y.; Hou, W.; Zhang, X. Adv. Synth. Catal. 2017, 359, 4399.
[64] Liu, X. X.; Wu, Z. Y.; He, Y. Q.; Zhou, X. Q.; Hu, T.; Ma, C. W.; Huang, G. S. Adv. Synth. Catal. 2016, 358, 2385.
[65] Chen, C.; Zhu, M. H.; Jiang, L. H.; Zeng, Z. B.; Yi, N. N.; Xiang, J. N. Org. Biomol. Chem. 2017, 15, 8134.
[66] Daggupati, R.; Malapak, C. Org. Chem. Front. 2018, 5, 788.
[67] Liu, X.; Pu, J.; Luo, X.; Cui, X.; Wu, Z.; Huang, G. Org. Chem. Front. 2018, 5, 361.
[68] (a) Povarov, L. S.; Mikhailov, B. M. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1963, 953.
(b) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1963, 2039.
[69] Richter, H.; García Mancheño, O. Org. Lett. 2011, 13, 6066.
[70] Liu, P.; Wang, Z.; Lin, J.; Hu, X. Eur. J. Org. Chem. 2012, 1583.
[71] Rohlmann, R.; Stopka, T.; Richter, H.; Mancheño, O. J. Org. Chem. 2013, 78, 6050.
[72] Jia, X.; Peng, F.; Qing, C.; Huo, C.; Wang, X. Org. Lett. 2012, 14, 4030.
[73] Jia, X.; Huo, W.; Shao, Y.; Yuan, Y.; Chen, Q.; Li, P.; Liu, X.; Ji, H. Chem.-Eur. J. 2017, 23, 12980.
[74] Jia, X. D.; Wang, Y.; Peng, F.; Huo, C.; Yu, L.; Liu, J.; Wang, X. Adv. Synth. Catal. 2014, 356, 1210.
[75] (a) Bolm, C.; Legros, J.; Le Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217.
(b) Bauer, I.; Knölker, H. J. Chem. Rev. 2015, 115, 3170.
[76] Li, Z.; Cao, L.; Li, C. J. Angew. Chem., Int. Ed. 2007, 46, 6505.
[77] Huo, C.; Chen, F.; Yuan, Y.; Xie, H.; Wang, Y. Org. Lett. 2015, 17, 5028.
[78] Huo, C.; Yuan, Y.; Chen, F.; Wang, Y. Adv. Synth. Catal. 2015, 357, 3648.
[79] Huo, C.; Xie, H.; Chen, F.; Tang, J.; Wang, Y. Adv. Synth. Catal. 2016, 358, 724.
[80] Wei, W. T.; Li, H. B.; Song, R. J.; Li, J. H. Chem. Commun. 2015, 51, 11325.
[81] (a) Jia, X.; Wang, Y.; Peng, F.; Huo, C.; Yu, L.; Liu, J.; Wang, X. J. Org. Chem. 2013, 78, 9450.
(b) Wang, Y.; Peng, F.; Liu, J.; Huo, C.; Wang, X.; Jia, X. J. Org. Chem. 2015, 80, 609.
(c) Liu, J.; Wang, Y.; Yu, L.; Huo, C.; Wang, X.; Jia, X. Adv. Synth. Catal. 2014, 356, 3214.
(d) Liu, G.; Quian, J.; Hua, J.; Cai, F.; Li, X.; Liu, L. Org. Biomol. Chem. 2016, 14, 1147.
(e) Xie, Z.; Jia, J.; Liu, X.; Liu, L. Adv. Synth. Catal. 2016, 358, 919.
(e) Ni, M.; Zhang, Y.; Gong, T.; Feng, B. Adv. Synth. Catal. 2017, 359, 824.
(f) Yang, X.; Li, L.; Li, Y.; Zhang, Y. J. Org. Chem. 2016, 81, 12433.
(g) Liu, X.; Shao, Y.; Li, P.; Ji, H.; Yuan, Y.; Jia, X. Tetrahedron Lett. 2018, 59, 637.
(h) Meng, Q. Y.; Gao, X. W.; Lei, T.; Liu, Z.; Zhan, F.; Li, Z. J.; Zhong, J. J.; Xiao, H.; Feng, K.; Chen, B.; Tao, Y.; Tung, C. H.; Wu, L. Z. Sci. Adv. 2017, 3, e1700666.
[82] Deng, Q. H.; Zou, Y. Q.; Lu, L. Q.; Tang, Z. L.; Chen, J. R.; Xiao, W. J. Chem.-Asian J. 2014, 9, 2432.
[83] Li, Y. J.; Li, X.; Zhang, S. X.; Zhao, Y. L.; Liu, Q. Chem. Commun. 2015, 51, 11565.
[84] Huo, C.; Yuan, Y.; Chen, F.; Tang, J.; Wang, Y. Org. Lett. 2015, 17, 4208.
[85] Xie, J.; Huang, Y.; Song, H.; Liu, Y.; Wang, Q. Org. Lett. 2017, 19, 6056.
[86] Li, H.; Huang, S.; Wang, Y.; Huo, C. Org. Lett. 2018, 20, 92.
[87] Tang, L.; Li, X. M.; Matuska, J. H.; He, Y. H.; Guan, Z. Org. Lett. 2018, 20, 5618.

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