Application of Organocatalysis in Asymmetric Construction of Nitrogen-Containing Heterocyclic Compounds

doi:10.6023/cjoc202008037

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 1-11.DOI: 10.6023/cjoc202008037 Previous Articles Next Articles

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有机催化在不对称构建含氮杂环化合物中的应用

郑雨^a, 谢珍珍^a, 陈凯^a, 向皞月^a^,^*(), 阳华^a^,^*()

a 中南大学化学化工学院长沙 410083

收稿日期:2020-08-20 修回日期:2020-09-22 发布日期:2020-10-12
通讯作者: 向皞月, 阳华

作者简介:

郑雨, 2012~2016年就读于中南大学化学化工学院, 获得学士学位; 2016~2019年就读于中南大学化学化工学院, 获得硕士学位; 2019年至今在中南大学化学化工学院阳华课题组攻读博士学位. 主要研究方向为有机小分子催化及新型有机小分子催化剂的设计、合成与应用.

谢珍珍, 2014~2018年就读于吉首大学化学化工学院, 获得学士学位; 2018年至今在中南大学化学化工学院阳华教授课题组攻读硕士学位. 主要研究方向为有机催化合成含氮含氧杂环.

陈凯, 博士, 讲师. 2005~2009年就读于南开大学药学院, 获得学士学位. 2009~2014年就读于北京大学化学化工学院, 获得理学博士学位, 师从吴云东教授和Olaf Wiest教授, 在表观遗传学调控蛋白与小分子的相互作用机制以及抑制剂设计方面取得了一定进展, 对组蛋白去乙酰化酶家族的选择性抑制提出了新的理论模型. 2015年加入华南理工大学化学化工学院祝诗发课题组从事博士后工作, 对过渡金属催化的烯炔醛环异构化反应机理进行了深入的理论研究. 2019年在韩国高等科学技术院Mookie Baik课题组进行访问研究. 2019年年底加入中南大学化学化工学院, 主要从事基于自由基中间体串联反应的机理研究以及新型有机催化剂的设计开发.

向皞月, 博士, 副教授, 硕士生导师. 2006~2010年就读于湖南师范大学化学化工学院, 获得学士学位. 2010~2015就读于中国科学院上海药物研究所, 获得博士学位, 在杂环化合物库的构建、苗子/先导化合物的发现取得了一定进展. 构建了基于色酮的含氮杂环小分子化合物库, 并从中发现了一些结构新颖的抗肿瘤先导化合物, 设计合成了系PI3K抑制剂, 在体外表现出良好的抗肿瘤活性. 2015年至今于中南大学化学化工学院承担有机化学、药物化学等教学工作, 并开展研究工作. 致力于光氧化还原催化体系研究以及含氮/氟杂环小分子化合物库构建新方法的开发.

阳华, 博士, 中南大学海外高层次人才“升华学者”特聘教授, 博士生导师. 1991~1995年就读于四川大学精细化工专业, 获得学士学位; 1996~1998年就读于四川大学有机化学专业, 获得硕士学位; 2001~2006就读于美国西弗吉尼亚大学, 获得博士学位; 2006~2011年在美国俄勒冈州立大学开展博士后研究工作, 并随后被提升为助理研究员独立开展研究工作; 2011年至今以中南大学“升华学者”特聘教授进入中南大学化学化工学院任教并开展研究工作. 主要从事有机合成和催化方面的研究, 重点在手性催化、光催化、复杂手性药物分子的合成与改性等领域取得了系列研究成果.

* Corresponding authors. E-mail: hyangchem@csu.edu.cn; xianghaoyue@csu.edu.cn

基金资助:
国家自然科学基金(Nos. 21576296); 国家自然科学基金(21776318); 国家自然科学基金(81703365); 资助项目.

Application of Organocatalysis in Asymmetric Construction of Nitrogen-Containing Heterocyclic Compounds

Yu Zheng^a, Zhenzhen Xie^a, Kai Chen,^a, Haoyue Xiang,^a^,^*(), Hua Yang,^a^,^*()

1 College of Chemistry and Chemical Engineering, Central South University, Changsha 410083

Received:2020-08-20 Revised:2020-09-22 Published:2020-10-12
Contact: Haoyue Xiang,, Hua Yang,
Supported by:
the National Natural Science Foundation of China(Nos. 21576296); the National Natural Science Foundation of China(21776318); the National Natural Science Foundation of China(81703365)

Nitrogen-containing heterocyclic structures are widely encountered in natural products and pharmaceuticals, which demonstrate broad-spectrum biological and pharmacological activities, and have attracted intensive attention from organic chemists and medicinal chemists. As a consequence, developing their green and efficient pathways, especially in asymmetric fashion, has always been a hot research field in the synthetic chemistry. In recent years, a series of organocatalysts based on amino acid such as proline and pyroglutamic acid have been reported, which have been well applied in the asymmetric construction of various nitrogen-containing compounds. This account mainly focuses on the research of asymmetric synthesis of nitrogen-containing heterocyclic compounds in our group, and the possible mechanisms of some typical reactions are thus discussed.

Key words: organocatalysis, asymmetric synthesis, N-heterocycle, proline, pyroglutamic acid

Cite this article

Yu Zheng, Zhenzhen Xie, Kai Chen,, Haoyue Xiang,, Hua Yang,. Application of Organocatalysis in Asymmetric Construction of Nitrogen-Containing Heterocyclic Compounds[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 1-11.

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Fig. & Tab. 9

Scheme 1. Representative chiral nitrogen-containing heterocyclic compounds

Scheme 2. Synthesis of prolinosulfonamide catalyst-Hua Cat

Scheme 3. Design of chiral catalysts from amino acid derivatives

Scheme 4. Activation mode of cyclohexenone by Hua Cat

Scheme 5. Transformation of chiral spirooxindole compounds

Scheme 6. Transformation of tetrahydrocarbazole

Scheme 7. Hua Cat-catalyzed asymmetric Michael addition reaction of azlactones

Scheme 8. Mechanistic studies

Scheme 9. Synthesis of chiral 3-hydrooxindole33 catalyzed by novelL-pyroglutamic acid derivatives

References 44

[1]	(a) Wang, S.-Q, Huang, W.-Y, Zhang, X.-R, Zhang, X.-T, Pan. C.-X. Chin. J. Org. Chem. 2020, 40, 959.
	( 王淑琴, 黄婉云, 张小蓉, 张晓婷, 潘成学, 有机化学, 2020, 40, 959.).
	(b) Li Q.; Wang Y.; Hu M.-J; Chen P.; You W.-W; Zhao P.-L. Chin. J. Org. Chem. 2017, 37, 967.
	( 黎秋, 汪雨, 胡孟金, 陈鹏, 游文玮, 赵培亮, 有机化学, 201 7, 37, 967.).
	(c) White N.J.; Pukrittayakamee S.; Phyo A.P.; Rueangweerayut R.; Nosten F.; Jittamala P.; Jeeyapant A.; Jain J.P.; Lefevre G.; Li R.; Magnusson B.; Diagana T.T.; Leong F.J. N. Engl. J. Med. 2014, 371, 403.
	(d) Witherup K.M.; Ransom R.W.; Graham A.C.; Bernard A.M.; Salvatore M.J.; Lumma W.C.; Anderson P.S.; Pitzenberger S.M.; Varga S.L. J. Am. Chem. Soc. 1995, 117, 6682.
	(e) Güller R.; Borschberg H.-J. Tetrahedron :Asymmetry 1992, 3, 1197.
[2]	Vitaku E.; Smith D.T.; Njardarson J.T. J. Med. Chem. 2014, 57, 10257.
[3]	Sun G.; Zhang, W.-W; Zhan, X.-P; Liu, Z.-L; Mao. Z.-M.Chin. J. Org. Chem. 2014, 34, 546.
	( 孙广龙, 张蔚蔚, 詹晓平, 刘增路, 毛振民, 有机化学, 2014, 34, 546.).
[4]	Smith M.C.; Riskin B.J. Drugs 1991, 42, 365.
[5]	(a) Jui N.T.; Garber J.A.; Finelli F.G.; MacMillan D.W. J. Am. Chem. Soc. 2012, 134, 11400.
	(b) Kwiatkowski P.; Beeson T.D.; Conrad J.C.; MacMillan D.W. J. Am. Chem. Soc. 2011, 133, 1738.
[6]	(a) Schreyer L.; Properzi R.; List B. Angew. Chem. Int. Ed. 2019, 58, 12761.
	(b) Ouyang J.; Kennemur J.L.; De C.K.; Fares C.; List B. J. Am. Chem. Soc. 2019, 141, 3414.
[7]	(a) Hu B.; Bezpalko M.W.; Fei C.; Dickie D.A.; Foxman B.M.; Deng L. J. Am. Chem. Soc. 2018, 140, 13913.
	(b) Tian S.-K.; Chen Y.; Hang J.; Tang L.; McDaid P.; Deng L. Acc. Chem. Res. 2004, 37, 621.
[8]	(a) Zhu Y.; Wang Q.; Cornwall R.G.; Shi Y. Chem. Rev. 2014, 114, 8199.
	(b) Wong O.A.; Shi Y. Chem. Rev. 2008, 108, 3958.
[9]	(a) Li Q.; Levi S.M.; Jacobsen E.N. J. Am. Chem. Soc. 2020, 142, 11865.
	(b) Doyle A.G.; Jacobsen E.N. Chem. Rev. 2007, 107, 5713.
[10]	(a) Dutartre M.; Bayardon J.; Juge S. Chem. Soc. Rev. 2016, 45, 5771.
	(b) James T.; van Gemmeren M.; List B. Chem. Rev. 2015, 115, 9388.
	(c) Melchiorre P.; Marigo M.; Carlone A.; Bartoli G. Angew. Chem. Int. Ed. 2008, 47, 6138.
	(d) Enders D.; Niemeier O.; Henseler A. Chem. Rev. 2007, 107, 5606.
	(e) Kunz R.K.; MacMillan. J. Am. Chem. Soc. 2005, 127, 3240.
[11]	(a) Wang L.; Liu J. Synthesis 2016, 49, 960.
	(b) Mukherjee S.; Yang J.W.; Hoffmann S.; List B. Chem. Rev. 2007, 107, 5471.
	(c) List B.; Lerner R.A.; Barbas C.F. J. Am. Chem. Soc. 2000, 122, 2395.
[12]	(a) Reyes-Rodriguez G.J.; Rezayee N.M.; Vidal-Albalat A.; Jorgensen K.A. Chem. Rev. 2019, 119, 4221.
	(b) Jensen K.L.; Dickmeiss G.; Jiang H.; Albrecht L.; Jorgensen K.A. Acc. Chem. Res. 2012, 45, 248.
[13]	Silvi M.; Verrier C.; Rey Y.P.; Buzzetti L.; Melchiorre P. Nat. Chem. 2017, 9, 868.
[14]	Hartikka A.; Arvidsson P.R. Tetrahedron : Asymmetry 2004, 15, 1831.
[15]	(a) Enders D.; Grondal C.; Huttl M.R. Angew. Chem. Int. Ed. 2007, 46, 1570.
	(b) Cordova A.; Watanabe S.; Tanaka F.; Notz W.; Barbas C.F. J. Am. Chem. Soc. 2002, 124, 1866.
[16]	Yang H.; Carter R.G. Org. Lett. 2008, 10, 4649.
[17]	Yang H.; Carter R.G. J. Org. Chem. 2009, 74, 2246.
[18]	(a) Zaminer J.; Brockmann C.; Huy P.; Opitz R.; Reuter C.; Beyermann M.; Freund C.; Muller M.; Oschkinat H.; Kuhne R.; Schmalz H.G. Angew. Chem. Int. Ed. 2010, 49, 7111.
	(b) Bateman L.; Breeden S.W.; O’Leary P. Tetrahedron: Asymmetry 2008, 19, 391.
[19]	Chen X.-Y.; Gao Z.-H.; Ye S. Acc. Chem. Res. 2020, 53, 690.
[20]	(a) Davies A.T.; Pickett P.M.; Slawin A.M.Z.; Smith A.D. ACS Catal. 2014, 4, 2696.
	(b) Massey R.S.; Collett C.J.; Lindsay A.G.; Smith A.D.; O'Donoghue A.C. J. Am. Chem. Soc. 2012, 134, 20421.
[21]	(a) Yarlagadda S.; Sankaram G.S.; Balasubramanian S.; Subba Reddy, B.V.Org. Lett. 2018, 20, 4195.
	(b) Liu H.; Cun L.-F.; Mi A.-Q.; Jiang Y.-Z.; Gong L.-Z. Org. Lett. 2006, 8, 6023.
[22]	(a) Banerjee T.S.; Paul S.; Sinha S.; Das S. Bioorg. Med. Chem. 2014, 22, 6062.
	(b) Wishka D.G.; Walker D.P.; Yates K.M.; Reitz S.C.; Jia S.; Myers J.K.; Olson K.L.; Jacobsen E.J.; Wolfe M.L.; Groppi V.E.; Hanchar A.J.; Thornburgh B.A.; Cortes-Burgos L.A.; Wong E.H.; Staton B.A.; Raub T.J.; Higdon N.R.; Wall T.M.; Hurst R.S.; Walters R.R.; Hoffmann W.E.; Hajos M.; Franklin S.; Carey G.; Gold L.H.; Cook K.K.; Sands S.B.; Zhao S.X.; Soglia J.R.; Kalgutkar A.S.; Arneric S.P.; Rogers B.N. J. Med. Chem. 2006, 49, 4425.
[23]	Liu H.; Cun L.F.; Mi A.Q.; Jiang Y.Z.; Gong L.Z. Org. Lett. 2006, 8, 6023.
[24]	Yang H.; Carter R.G. J. Org. Chem. 2009, 74, 5151.
[25]	(a) Nath R.; Pathania S.; Grover G.; Akhtar M.J. J. Mol. Struct. 2020, 1222, 128900.
	(b) Arun Y.; Saranraj K.; Balachandran C.; Perumal P.T. Eur. J. Med. Chem. 2014, 74, 50.
[26]	(a) Zhang L.-L.; Zhang J.-W.; Xiang S.-H.; Guo Z.; Tan B. Chin. J. Chem. 2018, 36, 1182.
	(b) Mei G.-J.; Shi F. Chem. Commun. 201 8, 54, 6607.
	(c) Tan F.; Xiao W.-J; Zeng G.-P. Chin. J. Org. Chem. 2017, 37, 824.
	( 谭芬, 肖文精, 曾国平, 有机化学, 201 7, 37, 824.).
	(d) Xiao, Y.-L; Zhou, Y.; Wang, J.; Wang, J.-X; Liu, H. Chin. J. Org. Chem. 2015, 35, 2035.
	( 肖永龙, 周宇, 王江, 王进欣, 柳红, 有机化学, 2015, 35, 2035.).
[27]	(a) Shi F.; Zhu R.-Y.; Liang X.; Tu S.-J. Adv. Synth. Catal. 2013, 355, 2447.
	(b) Chen X.-H.; Wei Q.; Luo S.-W.; Xiao H.; Gong L.-Z. J. Am. Chem. Soc. 2009, 131, 13819.
[28]	Shi F.; Tao Z.-L.; Luo S.-W.; Tu S.-J.; Gong L.-Z. Chem. Eur. J. 2012, 18, 6885.
[29]	Tian L.; Hu X.-Q.; Li Y.-H.; Xu P.-F. Chem. Commun. 2013, 49, 7213.
[30]	Xiao J.-A.; Liu Q.; Ren J.-W.; Liu J.; Carter R.G.; Chen X.-Q.; Yang H. Eur. J. Org. Chem. 2014, 2014, 5700.
[31]	Ren J.-W.; Zhou Z.-F.; Xiao J.-A.; Chen X.-Q.; Yang H. Eur. J. Org. Chem. 2016, 2016, 1264.
[32]	(a) Wang T.; Yu Z.; Hoon D.L.; Phee C.Y.; Lan Y.; Lu Y. J. Am. Chem. Soc. 2016, 138, 265.
	(b) Wei X.; Liu D.; An Q.; Zhang W. Org. Lett. 2015, 17, 5768.
	(c) Wang B.; Tu Y.Q. Acc. Chem. Res. 2011, 44, 1207.
[33]	(a) Alba A.N.; Rios R. Chem. Asian. J. 2011, 6, 720.
	(b) Fisk J.S.; Mosey R.A.; Tepe J.J. Chem. Soc. Rev. 2007, 36, 1432.
[34]	Zhang J.; Liu X.; Wu C.; Zhang P.; Chen J.; Wang R. Eur. J. Org. Chem. 2014, 2014, 7104.
[35]	Wei Y.; Liu Z.; Wu X.; Fei J.; Gu X.; Yuan X.; Ye J. Chem. Eur. J. 2015, 21, 18921.
[36]	Zhang S.-Y.; Ruan G.-Y.; Geng Z.-C.; Li N.-K.; Lv M.; Wang Y.; Wang X.-W. Org. Biomol. Chem. 201 5, 13, 5698.
[37]	Wang C.-M.; Xiao J.-A.; Wang J.; Wang S.-S.; Deng Z.-X.; Yang H. J. Org. Chem. 2016, 81, 8001.
[38]	(a) Gabriel I. Molecules 2020, 25, 1480.
	(b) Gensicka-Kowalewska M.; Cholewiński G.; Dzierzbicka K. RSC Adv. 2017, 7, 15776.
[39]	(a) Mayekar N.V.; Nayak S.K.; Chattopadhyay S. Synth. Commun. 2004, 34, 3111.
	(b) Jacob R.G.; Perin G.; Botteselle G.V.; Lenardão E.J. Tetrahedron Lett. 2003, 44, 6809.
[40]	(a) Chen M.-W.; Cai X.-F.; Chen Z.-P.; Shi L.; Zhou Y.-G. Chem. Commun. 2014, 50, 12526.
	(b) Dickmeiss G.; Jensen K.L.; Worgull D.; Franke P.T.; Jorgensen K.A. Angew. Chem. Int. Ed. 2011, 123, 1681.
[41]	Li S.; Wang J.; Xia P.-J.; Zhao Q.-L.; Wang C.-M.; Xiao J.-A.; Chen X.-Q.; Xiang H.-Y.; Yang H. J. Org. Chem. 2018, 83, 12284.
[42]	Ren J.-W.; Wang J.; Xiao J.-A.; Li J.; Xiang H.-Y.; Chen X.-Q.; Yang H. J. Org. Chem. 2017, 82, 6441.
[43]	Ren J.-W.; Zheng L.; Ye Z.-P.; Deng Z.-X.; Xie Z.-Z.; Xiao J.-A.; Zhu F.-W.; Xiang H.-Y.; Chen X.-Q.; Yang H. Org. Lett. 2019, 21, 2166.
[44]	Wang J.; Deng Z.-X.; Wang C.-M.; Xia P.-J.; Xiao J.-A.; Xiang H.-Y.; Chen X.-Q.; Yang H. Org. Lett. 2018, 20, 7535.

有机催化在不对称构建含氮杂环化合物中的应用

Application of Organocatalysis in Asymmetric Construction of Nitrogen-Containing Heterocyclic Compounds

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Fig. & Tab. 9

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