Recent Advances in Synthesis of Chiral 1,2-Dihydropyridines

doi:10.6023/A21040131

Acta Chimica Sinica ›› 2021, Vol. 79 ›› Issue (6): 685-693.DOI: 10.6023/A21040131 Previous Articles Next Articles

Review

手性1,2-二氢吡啶化合物的合成研究进展

穆博帅^a, 张志豪^a, 武文彪^a^,^*(), 余金生^a, 周剑^a^,^b^,^*()

a 华东师范大学化学与分子工程学院上海分子治疗与新药创制工程技术研究中心上海市绿色化学与化工过程绿色化重点实验室上海 200062
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

投稿日期:2021-04-02 发布日期:2021-05-20
通讯作者: 武文彪, 周剑

作者简介:

穆博帅, 男, 1990年生于河北保定. 2013年本科毕业于河北师范大学汇华学院; 2016年硕士毕业于河北师范大学化学与材料科学学院, 随后加入华东师范大学周剑教授课题组攻读博士学位, 主要从事不对称催化的串联反应设计与研究.

张志豪, 男, 1994年生于陕西咸阳. 2017年本科毕业于北京化工大学化学工程与工艺专业, 随后加入华东师范大学周剑教授课题组攻读硕士学位, 主要从事二氧化碳参与的不对称催化反应研究.

武文彪, 男, 1992年生于河南安阳. 2015年本科毕业于河南大学, 随后加入华东师范大学周剑教授课题组, 并于2020年7月获得有机化学博士学位. 2020年9月至今在华东师范大学进行博士后研究, 主要从事不对称氰化反应研究.

余金生, 华东师范大学化学与分子工程学院青年研究员, 博士生导师. 2011年于江西师范大学本科毕业后加入华东师范大学周剑教授课题组, 并于2016年获理学博士学位. 随后在日本微生物化学研究所Masakatsu Shibasaki教授课题组进行JSPS博士后研究. 于2019年初加入华东师范大学, 目前研究兴趣主要是含氟手性化合物的不对称催化合成及其在药物研究中的应用.

周剑, 华东师范大学化学与分子工程学院教授, 博士生导师. 本科毕业于四川师范大学; 2004年毕业于中国科学院上海有机化学研究所, 获理学博士学位; 先后在日本东京大学Shu Kobayashi和德国马普煤炭研究所Benjamin List课题组从事博士后研究后, 于2008年底加入华东师范大学. 研究兴趣在于立足协同催化的理念, 结合新催化剂和新试剂的设计开发, 发展导向具有手性季碳的药物优势骨架的不对称催化构建新方法.

基金资助:
国家自然科学基金(21971067); 上海市“科技创新行动计划”(20JC1416900)

Recent Advances in Synthesis of Chiral 1,2-Dihydropyridines

Bo-Shuai Mu^a, Zhi-Hao Zhang^a, Wen-Biao Wu^a(), Jin-Sheng Yu^a, Jian Zhou^a^,^b()

a Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032, China

Received:2021-04-02 Published:2021-05-20
Contact: Wen-Biao Wu, Jian Zhou
Supported by:
National Natural Science Foundation of China(21971067); Shanghai Science and Technology Innovation Action Plan(20JC1416900)

Chiral 1,2-dihydropyridines represent a class of versatile building blocks that can undergo diversifying reactions of conjugated dienes such as reduction or cycloaddition reaction, allowing facile synthesis of chiral piperidines and other nitrogen-containing heterocycles, prominent structural motifs in drugs and bioactive compounds. The efficient synthesis of chiral 1,2-dihydropyridines is highly desirable and beneficial for the drug discovery and development. The chiral pool strategy and chiral auxiliary based synthesis require the use of stoichiometric chiral reagents, so it is much sought-after to develop catalytic asymmetric methods to synthesize structurally diverse chiral 1,2-dihydropyridines. Since the pioneering catalytic enantioselective addition of nucleophiles to the C2 position of achiral activated pyridine derivatives in 2004, this strategy has been successfully employed for the catalytic synthesis of optically active 1,2-dihydropyridines bearing an aryl, alkyl or alkynyl group at the C2 position. Recently, tandem sequences was reported based on the asymmetric conversion of C=N bonds as an emerging strategy for the synthesis of multisubstituted chiral 1,2-dihydropyridines. This review summarizes the advances in this field, and discusses the challenges and synthetic opportunities for future development.

Key words: chiral 1,2-dihydropyridine, chiral amine, chiral auxiliary, asymmetric catalysis

Cite this article

Bo-Shuai Mu, Zhi-Hao Zhang, Wen-Biao Wu, Jin-Sheng Yu, Jian Zhou. Recent Advances in Synthesis of Chiral 1,2-Dihydropyridines[J]. Acta Chimica Sinica, 2021, 79(6): 685-693.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 23

Figure 1. Some drugs containing piperidine and pyridine structures

Figure 2. Importance of chiral 1,2-dihydropyridine compounds

Figure 3. Synthetic strategies of chiral 1,2-dihydropyridines

Figure 4. Synthesis of chiral 1,2-dihydropyridines from L-lysine derivatives

Figure 5. Syntheses of 1,2-dihydropyridines from L-alanine and L-phenylalanine derivatives

Figure 6. Asymmetric nucleophilic addition induced by menthol derivatives

Figure 7. Asymmetric nucleophilic addition induced by L-valinol derivatives

Figure 8. Total synthesis of (–)-L-733061

Figure 9. Asymmetric catalytic syntheses of chiral 1,2-dihydropyridines

Figure 10. Asymmetric catalytic Reissert reaction of 18

Figure 11. Asymmetric catalytic Reissert reaction of quinoline and isoquinoline derivatives

Figure 12. Asymmetric nucleophilic addition of alkynes and pyridine derivatives

Figure 13. Asymmetric nucleophilic addition of quinoline derivatives 31 and alkynes 32

Figure 14. Asymmetric nucleophilic addition of organoboronic acids to pyridine derivatives 34

Figure 15. Asymmetric addition of organoboronic acids to 38

Figure 16. Asymmetric addition of organoboronic acids to quinolines

Figure 17. Cu-catalyzed asymmetric nucleophilic addition of zinc reagents to pyridine derivatives

Figure 18. Ni-catalyzed asymmetric nucleophilic addition using zinc reagents to 4-methoxypyridine

Figure 19. Ni-catalyzed asymmetric nucleophilic addition using zinc reagents to pyridine

Figure 20. Addition reaction using silyl enol ether to pyridine derivatives 56

Figure 21. Asymmetric [3+2] cycloaddition

Figure 22. Asymmetric Mannich/Wittig/cycloisomerization sequence

Figure 23. Product derivatization

References 33

[1]	(a) Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J. Med. Chem. 2014, 57, 5845. doi: 10.1021/jm4017625
	(b) Majumdar, K. C. Heterocycles in Natural Product Synthesis, Wiley-VCH, Weinheim, 2011.
	(c) Alvarez-Builla, J.; Vaquero, J. J.; Barluenga, J. Modern Heterocyclic Chemistry, Wiley-VCH, Weinheim, 2011.
	(d) Zhao, J.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235. (in Chinese) doi: 10.6023/A15010063
	(赵金钵, 张前, 化学学报, 2015, 73, 1235.) doi: 10.6023/A15010063
	(e) Wang, Y.; Liu, Y. Acta Chim. Sinica 2019, 77, 418. (in Chinese) doi: 10.6023/A19020061
	(王昱赟, 刘云云, 化学学报, 2019, 77, 418.) doi: 10.6023/A19020061
	(f) Zheng, Y.; Xie, Z.; Chen, K.; Xiang, H.; Yang, H. Chin. J. Org. Chem. 2021, 41, 1. (in Chinese) doi: 10.6023/cjoc202008037
	(郑雨, 谢珍珍, 陈凯, 向皞月, 阳华, 有机化学, 2021, 41, 1.) doi: 10.6023/cjoc202008037
	(g) Zhang, J.; Liu, P.; Sun, P. Chin. J. Org. Chem. 2021, 41, 185. (in Chinese) doi: 10.6023/cjoc202006010
	(张杰, 刘平, 孙培培, 有机化学, 2021, 41, 185.) doi: 10.6023/cjoc202006010
[2]	(a) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b
	(b) Zhang, B.; Zhou, Q.; Chen, R.; Jiang, H. Chin. J. Org. Chem. 2012, 32, 1653. (in Chinese) doi: 10.6023/cjoc1201291
	(张斌, 周其忠, 陈仁尔, 蒋华江, 有机化学, 2012, 32, 1653.) doi: 10.6023/cjoc1201291
[3]	(a) Shankaraiah, N.; Pilli, R. A.; Santos, L. S. Tetrahedron Lett. 2008, 49, 5098. doi: 10.1016/j.tetlet.2008.06.028
	(b) Xiao, D.; Lavey, B. J.; Palani, A.; Wang, C.; Aslanian, R. G.; Kozlowski, J. A.; Shih, N.-Y.; McPhail, A. T.; Randolph, G. P.; Lachowicz, J. E.; Duffy, R. A. Tetrahedron Lett. 2005, 46, 7653. doi: 10.1016/j.tetlet.2005.08.148
	(c) Kato, A.; Kato, N.; Kano, E.; Adachi, I.; Ikeda, K.; Yu, L.; Okamoto, T.; Banba, Y.; Ouchi, H.; Takahata, H.; Asano, N. J. Med. Chem. 2005, 48, 2036. doi: 10.1021/jm0495881
	(d) Janssen, P. A. J. Br. J. Anaesth. 1962, 34, 260. doi: 10.1093/bja/34.4.260
[4]	(a) Sperber, N.; Papa, D. J. Am. Chem. Soc. 1949, 71, 887. doi: 10.1021/ja01171a034 pmid: 11831902
	(b) Leader, H.; Wolfe, A. D.; Chiang, P. K.; Gordon, R. K. J. Med. Chem. 2002, 45, 902. pmid: 11831902
	(c) Sperber, N.; Papa, D. J. Am. Chem. Soc. 1949, 71, 887. doi: 10.1021/ja01171a034 pmid: 11831902
	(d) Prieri, M.; Frita, R.; Probst, N.; Sournia-Saquet, A.; Bourotte, M.; Deprez, B.; Baulard, A. R.; Willand, N. Eur. J. Med. Chem. 2018, 159, 35. doi: 10.1016/j.ejmech.2018.09.038 pmid: 11831902
[5]	(a) Allais, C.; Grassot, J.-M.; Rodriguez, J.; Constantieux, T. Chem. Rev. 2014, 114, 10829. doi: 10.1021/cr500099b
	(b) Henry, G. D. Tetrahedron 2004, 60, 6043. doi: 10.1016/j.tet.2004.04.043
[6]	Selected reviews: (a) Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1. doi: 10.1021/cr60275a001
	(b) Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223. doi: 10.1021/cr00048a004
	(c) Nebe, M. M.; Opatz, T. Adv. Heterocycl. Chem. 2017, 122, 191.
[7]	(a) Bull, J. A.; Mousseau, J. J.; Pelletier, G.; Charette, A. B. Chem. Rev. 2012, 112, 2642. doi: 10.1021/cr200251d
	(b) Silva, E. M. P.; Varandas, P. A. M. M.; Silva, A. M. S. Synthesis 2013, 45, 3053. doi: 10.1055/s-00000084
[8]	(a) Yedoyan, J.; Wurzer, N.; Klimczak, U.; Ertl, T.; Reiser, O. Angew. Chem. Int. Ed. 2019, 58, 3594. doi: 10.1002/anie.201813716
	(b) Trost, B. M.; Biannic, B. Org. Lett. 2015, 17, 1433. doi: 10.1021/acs.orglett.5b00279
[9]	(a) Silva, E. M. P.; Rocha, D. H. A.; Silva, A. M. S. Synthesis 2018, 50, 1773. doi: 10.1055/s-0037-1609418
	(b) Menichetti, A.; Berti, F.; Pineschi, M. Molecules 2020, 25, 563. doi: 10.3390/molecules25030563
[10]	Khan, M. O. F.; Levi, M. S.; Clark, C. R.; Ablordeppey, S. Y.; Law, S.-L.; Wilson, N. H.; Borne, R. F. Stud. Nat. Prod. Chem. 2008, 34, 753.
[11]	Shono, T.; Matsumura, Y.; Onomura, O.; Yamada, Y. Tetrahedron Lett. 1987, 28, 4073. doi: 10.1016/S0040-4039(01)83864-8
[12]	Monguchi, D.; Majumdar, S.; Kawabata, T. Heterocycles 2006, 68, 2571. doi: 10.3987/COM-06-10883
[13]	Wu, P.; Wang, Q.-F.; Cai, X.-M.; Yan, C.-G. Chin. J. Org. Chem. 2008, 28, 1899. (in Chinese)
	(吴萍, 王琦芳, 蔡习美, 颜朝国, 有机化学, 2008, 28, 1899.)
[14]	Comins, D. L.; Hong, H.; Salvador, J. M. J. Org. Chem. 1991, 56, 7197. doi: 10.1021/jo00026a004
[15]	Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829. pmid: 11716753
[16]	Lemire, A.; Grenon, M.; Pourashraf, M.; Charette, A. B. Org. Lett. 2004, 6, 3517. doi: 10.1021/ol048624n
[17]	Ichikawa, E.; Suzuki, M.; Yabu, K.; Albert, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 11808. pmid: 15382912
[18]	Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6327. doi: 10.1021/ja0010352
[19]	Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 6801. pmid: 11448184
[20]	Sun, Z.; Yu, S.; Ding, Z.; Ma, D. J. Am. Chem. Soc. 2007, 129, 9300. doi: 10.1021/ja0734849
[21]	Pappoppula, M.; Cardoso, F. S. P.; Garrett, B. O.; Aponick, A. Angew. Chem. Int. Ed. 2015, 54, 15202. doi: 10.1002/anie.201507848
[22]	Nadeau, C.; Aly, S.; Belyk, K. J. Am. Chem. Soc. 2011, 133, 2878. doi: 10.1021/ja111540g
[23]	Robinson, D. J.; Spurlin, S. P.; Gorden, J. D.; Karimov, R. R. ACS Catal. 2020, 10, 51. doi: 10.1021/acscatal.9b03874
[24]	Wang, Y.; Liu, Y.; Zhang, D.; Wei, H.; Shi, M.; Wang, F. Angew. Chem. Int. Ed. 2016, 55, 3776. doi: 10.1002/anie.201511663
[25]	Yamaoka, Y.; Miyabe, H.; Takemoto, Y. J. Am. Chem. Soc. 2007, 129, 6686. doi: 10.1021/ja071470x
[26]	(a) Fernández-Ibáñez, M.Á.; Maciá, B.; Pizzuti, M. G.; Minnaard, A. J.; Feringa, B. L. Angew. Chem. Int. Ed. 2009, 48, 9339.
	(b) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. J. Org. Chem. 1993, 58, 7732. doi: 10.1021/jo00079a018
[27]	Chau, S. T.; Lutz, J. P.; Wu, K.; Doyle, A. G. Angew. Chem. Int. Ed. 2013, 52, 9153.
[28]	Lutz, J. P.; Chau, S. T.; Doyle, A. G. Chem. Sci. 2016, 7, 4105.
[29]	Mancheño, O. G.; Asmus, S.; Zurro, M.; Fischer, T. Angew. Chem. Int. Ed. 2015, 54, 8823.
[30]	Zhang, D.; Lin, L.; Yang, J.; Liu, X.; Feng, X. Angew. Chem. Int. Ed. 2018, 57, 12323.
[31]	Zhang, D.; Su, Z.; He, Q.; Wu, Z.; Zhou, Y.; Pan, C.; Liu, X.; Feng, X. J. Am. Chem. Soc. 2020, 142, 15975.
[32]	Mu, B.-S.; Cui, X.-Y.; Zeng, X.-P.; Yu, J.-S.; Zhou, J. Nat. Commun. 2021, 12, 2219.
[33]	The development of sustainable tandem reactions by internally reusing waste to promote the next step offers a new opportunity to develop new chemistry aiming at maximizing the atom utilization of a process. The current research showed that waste of previous step (including by-product, excess reagent and residual catalyst) could be internally reused as additive, catalyst or reagent to promote the next step. Advances of "waste as additive" tandem reactions: (a) Kinoshita, T.; Okada, S.; Park, S.-R.; Matsunaga, S.; Shibasaki, M. Angew. Chem. Int. Ed. 2003, 42, 4680.
	(b) Yu, T.-Y.; Wei, H.; Luo, Y.-C.; Wang, Y.; Wang, Z.-Y.; Xu, P.-F. J. Org. Chem. 2016, 81, 2730.
	(c) Gao, X.-T.; Gan, C.-C.; Liu, S.-Y.; Zhou, F.; Wu, H.-H.; Zhou, J. ACS Catal. 2017, 7, 8588.
	Advances of "waste as catalyst" tandem reactions: (d) Nishimoto, Y.; Yasuda, M.; Baba, A. Org. Lett. 2007, 9, 4931.
	(e) Alaimo, P. J.; O’Brien, R.; Johnson, A. W.; Slauson, S. R.; O’Brien, J. M.; Tyson, E. L.; Marshall, A.-L.; Ottinger, C. E.; Chacon, J. G.; Wallace, L.; Paulino, C. Y.; Connell, S. Org. Lett. 2008, 10, 5111.
	(f) Li, H.-H.; Dong, D.-J.; Jin, Y.-H.; Tian, S.-K. J. Org. Chem. 2009, 74, 9501.
	(g) Yang, B.-L.; Weng, Z.-T.; Yang, S.-J.; Tian, S.-K. Chem. Eur. J. 2010, 16, 718.
	(h) Cao, J.-J.; Zhou, F.; Zhou, J. Angew. Chem. Int. Ed. 2010, 49, 4976.
	(i) Gao, M.; Yang, Y.; Wu, Y.-D.; Deng, C.; Shu, W.-M.; Zhang, D.-X.; Cao, L.-P.; She, N.-F.; Wu, A.-X. Org. Lett. 2010, 12, 4026.
	(j) Lu, J.; Toy, P. H. Chem. Asian J. 2011, 6, 2251.
	(k) Teng, Y.; Lu, J.; Toy, P. H. Chem. Asian J. 2012, 7, 351.
	(l) Chen, L.; Shi, T.-D.; Zhou, J. Chem. Asian J. 2013, 8, 556.
	(m) Portalier, F.; Bourdreux, F.; Marrot, J.; Moreau, X.; Coeffard, V.; Greck, C. Org. Lett. 2013, 15, 5642.
	(n) Chen, L.; Du, Y.; Zeng, X.-P.; Shi, T.-D.; Zhou, F.; Zhou, J. Org. Lett. 2015, 17, 1557.
	(o) Zeng, X.-P.; Cao, Z.-Y.; Wang, X.; Chen, L.; Zhou, F.; Zhu, F.; Wang, C.-H.; Zhou, J. J. Am. Chem. Soc. 2016, 138, 416.
	Advances of "waste as reagent" tandem reactions: (p) Zhu, F.; Xu, P.-W.; Zhou, F.; Wang, C.-H.; Zhou, J. Org. Lett. 2015, 17, 972.
	(q) Liu, Y.-L.; Yin, X.-P.; Zhou, J. Chin. J. Chem. 2018, 36, 321.
	(r) Li, D.; Tan, Y.; Peng, L.; Li, S.; Zhang, N.; Liu, Y.; Yan, H. Org. Lett. 2018, 20, 4959.
	(s) Guo, Y.; Meng, C.; Liu, X.; Li, C.; Xia, A.; Xu, Z.; Xu, D. Org. Lett. 2018, 20, 913.

手性1,2-二氢吡啶化合物的合成研究进展

Recent Advances in Synthesis of Chiral 1,2-Dihydropyridines

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 23

References 33

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Zhanglong Yu, Zhongliang Li, Changjiang Yang, Qiangshuai Gu, Xinyuan Liu. Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols^★ [J]. Acta Chimica Sinica, 2023, 81(8): 955-966.
[2]	Shuang Yang, Ningyi Wang, Qingqing Hang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides^★ [J]. Acta Chimica Sinica, 2023, 81(7): 793-808.
[3]	Wang Rui-Xiang, Zhao Qing-Ru, Gu Qing, You Shu-Li. Gold/Iridium Catalyzed Alkynylamide Cyclization/Asymmetric Allylic Benzylation Cascade Reaction^★ [J]. Acta Chimica Sinica, 2023, 81(5): 431-434.
[4]	Qingduan Meng, Jiahong Han, Yixiao Pan, Wei Hao, Qing-Hua Fan. Asymmetric Synthesis of C₁-Symmetric Chiral N-Heterocyclic Carbene (NHC) Ligands and Their Applications in Asymmetric Catalysis^★ [J]. Acta Chimica Sinica, 2023, 81(10): 1271-1279.
[5]	Lai Zhang, Jian Xiao, Yawen Wang, Yu Peng. Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes [J]. Acta Chimica Sinica, 2022, 80(8): 1152-1164.
[6]	Jinyue Ma, Lufei Huang, Baowen Zhou, Lin Yao. Construction and Catalysis Advances of Inorganic Chiral Nanostructures [J]. Acta Chimica Sinica, 2022, 80(11): 1507-1523.
[7]	Qing-Ru Zhao, Ru Jiang, Shu-Li You. Ir-catalyzed Sequential Asymmetric Allylic Substitution/Olefin Isomerization for the Synthesis of Axially Chiral Compounds [J]. Acta Chimica Sinica, 2021, 79(9): 1107-1112.
[8]	Yi Li, Ming-Hua Xu. Applications of Asymmetric Petasis Reaction in the Synthesis of Chiral Amines [J]. Acta Chimica Sinica, 2021, 79(11): 1345-1359.
[9]	Wang Qiang, Gu Qing, You Shu-Li. Recent Progress on Transition-Metal-Catalyzed Asymmetric C-H Bond Functionalization for the Synthesis of Biaryl Atropisomers [J]. Acta Chim. Sinica, 2019, 77(8): 690-704.
[10]	Zhou Yuanchun, Zhou Zhi, Du Wei, Chen Yingchun. Asymmetric Inverse-Electron-Demand Diels-Alder Reaction of 2-Pyrone and 2,5-Dienones via HOMO-Activation [J]. Acta Chim. Sinica, 2018, 76(5): 382-386.
[11]	Li Shu-Sen, Wang Jianbo. Recent Advance in Asymmetric Trifluoromethylthiolation [J]. Acta Chim. Sinica, 2018, 76(12): 913-924.
[12]	Lu Hong, Liu Jin-Yu, Li Hong-Yu, Xu Peng-Fei. Recent Developments in N-Heterocyclic Carbene and Transition-Metal Cooperative Catalysis [J]. Acta Chim. Sinica, 2018, 76(11): 831-837.
[13]	Li Sujia, Lü Jian, Luo Sanzhong. Enantioselective Indium(I)/Chiral Phosphoric Acid-catalyzed[4+2] Cycloaddition of Simple Olefin and β,γ-Unsaturated α-Keto Esters [J]. Acta Chim. Sinica, 2018, 76(11): 869-873.
[14]	Zhou Xiao-Le, Su Yong-Liang, Wang Pu-Sheng, Gong Liu-Zhu. Asymmetric Allylic C-H Alkylation of 1,4-Dienes with Aldehydes [J]. Acta Chim. Sinica, 2018, 76(11): 857-861.
[15]	Yu Yue-Na, Xu Ming-Hua. Chiral Phosphorus-Olefin Ligands for Asymmetric Catalysis [J]. Acta Chim. Sinica, 2017, 75(7): 655-670.