手性胺/金(I)协同催化的不对称串联反应研究

doi:10.6023/cjoc202209016

摘要/Abstract

协同催化是改善反应效率和选择性控制的一种有力策略. 通过组合不同催化剂来获得协同效应, 实现单一催化剂难以企及的高反应活性和选择性以及发展挑战性新反应, 是不对称催化的重要研究内容. 手性胺根据胺结构的不同, 可通过烯胺、亚胺或攫氢活化等方式来活化具有α-氢的醛(酮)、共轭烯醛(酮)、活泼次甲基或亚甲基化合物; 而阳离子型的一价金催化可以高效活化烯烃、炔烃和重氮化合物, 因此, 结合两种催化剂的特点来发展不对称串联反应, 实现从简单原料出发构建较复杂手性化合物受到关注. 本综述旨在介绍手性伯胺、仲胺或叔胺与一价金协同催化来实现的不对称串联反应, 重点关注两者协同催化的优势、避免催化剂失活的方法以及讨论未来的发展空间, 进而为从事不对称催化相关的研究人员提供一些有益参考和借鉴.

关键词: 不对称催化, 协同催化, 手性胺催化, 金催化

Cooperative catalysis is a powerful strategy to improve the efficiency and selectivity of organic reactions. It is of current interest in asymmetric catalysis to combine different catalysts to secure synergistic effects to realize high reaction activity and selectivity unattainable by a single catalyst, and to develop challenging new reactions. Depending on their structures, chiral amines can activate aldehydes or ketones with α-protons, conjugated enals or enones, activated methine or methylene compounds via enamine catalysis, iminium catalysis or deprotonative activation. On the other hand, cationic gold(I) catalysis can efficiently activate olefins, alkynes or diazo compounds for functionalization reactions. Therefore, it has attracted ever-increasing attention to combine the reactivity patterns of the two types of catalysts to develop asymmetric tandem reactions, and paves a facile way to construct complex chiral compounds from simple starting materials. The purpose of this review is to introduce the asymmetric tandem reactions achieved by chiral amine & gold(I) catalysis, focusing on the advantages of such type of cooperative catalysis, the way to avoid catalyst deactivation, as well as its future development, so as to provide some useful references for researchers engaged in asymmetric catalysis.

Key words: asymmetric catalysis, cooperative catalysis, chiral amine catalysis, gold catalysis

引用此文

崔效源, 周锋, 吴海虹, 周剑. 手性胺/金(I)协同催化的不对称串联反应研究[J]. 有机化学, 2022, 42(10): 3033-3050.

Xiaoyuan Cui, Feng Zhou, Haihong Wu, Jian Zhou. Asymmetric Tandem Reactions Achieved by Chiral Amine & Gold(I) Cooperative Catalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3033-3050.

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图/表 22

图式1. 催化剂组合实现的协同催化

Scheme 1. Multiple catalysts realized cooperative catalysis

图式2. 有机胺&金协同催化

Scheme 2. Cooperative amine & Au catalysis

图式3. 不对称Michael加成/5-exo-dig环化反应合成双环烯酮衍生物

Scheme 3. Enantioselective Michael addition/5-exo-dig cyclization to bicyclic enones

图式4. 不对称Diels-Alder/5-exo-dig串联反应合成并环烯酮衍生物

Scheme 4. Enantioselective Diels-Alder/5-exo-dig cyclization reaction to [6,5,6]-carbocyclic enones

图式5. 不对称Diels-Alder/7-endo-dig串联反应合成多环吡咯衍生物

Scheme 5. Enantioselective Diels-Alder/7-endo-dig cyclization reaction to annulated pyrroles.

图式6. 不对称Michael加成/5-exo-dig环化串联反应合成手性四氢呋喃衍生物

Scheme 6. Enantioselective Michael addition/5-exo-dig cyclization to tetrahydrofuranyl

图式7. 不对称Michael加成/6-endo-dig环化串联反应合成双环缩醛

Scheme 7. Enantioselective Michael addition/6-endo-dig cyclization to bicyclic O,O-acetals.

图式8. 不对称α-烯丙基烷基化反应合成环状醛类衍生物

Scheme 8. Enantioselective α-allylic alkylation reaction to cyclic aldehyde

图式9. α-支链醛参与的不对称分子间α-烯丙基烷基化反应

Scheme 9. Enantioselective intermolecular α-allylic alkylation of α-branched aldehyde

图式10. 不对称Michael加成/5-exo-dig环化串联反应合成环戊烯醛

Scheme 10. Enantioselective Michael addition/5-exo-dig cyclization reaction to cyclopentene carbaldehydes

图式11. 不对称Michael加成/5-endo-dig环化串联反应合成丁烯酸内酯

Scheme 11. Enantioselective Michael addition/5-endo-dig cyclization reaction to butenolides

图式12. 不对称Diels-Alder/5-endo-dig环化反应合成呋喃并哌啶化合物

Scheme 12. Enantioselective Diels-Alder/5-endo-dig cyclization reaction to tetrahydrofuro[3-b]pyridines

图式13. 不对称Mannich/氢胺化反应合成二氢吡咯衍生物

Scheme 13. Enantioselective Mannich/hydroamination to dihydropyrrole

图式14. 不对称Mannich/氢胺化串联反应合成螺环氧化吲哚衍生物

Scheme 14. Enantioselective Mannich/hydroamination reaction to spirocyclic oxindoles.

图式15. 不对称Mannich/氢胺化串联反应合成四氢吡啶或四氢吡咯衍生物

Scheme 15. Enantioselective Mannich/hydroamination reaction to tetrahydropyridines or tetrahydropyrrole

图式16. 不对称Mannich/氢胺化串联反应合成双螺环氧化吲哚衍生物

Scheme 16. Enantioselective Mannich/hydroamination reaction to bispirocyclic oxindoles

图式17. 不对称亲核加成/氢胺化串联反应合成三螺环氧化吲哚衍生物

Scheme 17. Enantioselective nucleophilic addition/hydroamination reaction to trispirocyclic oxindoles

图式18. 碳氢键插入/Michael加成串联反应合成氧化吲哚衍生物

Scheme 18. C—H insertion/Michael addition to chiral oxindole

图式19. 烯酮形成/硅氰化串联反应合成氧化吲哚衍生物

Scheme 19. Enone-formation/cyanosilylation to chiral oxindoles

图式20. 烯基化/Michael/Michael串联反应合成螺环氧化吲哚衍生物

Scheme 20. Alkenylation/Michael/Michael to chiral spirocyclic oxindoles

图式21. 形式烯丙基化/Michael串联反应合成苯并噻吩酮衍生物

Scheme 21. Formal allylation/Michael to chiral benzothiophen-2-ones

图式22. 不对称hetero-ene反应合成氧化吲哚衍生物

Scheme 22. Enantioselective hetero-ene reaction to chiral oxindoles

参考文献 57

[1]	(a) Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, C. G. Chem. Rev. 2005, 105, 1001. doi: 10.1021/cr020018n
	(b) Denard, C. A.; Hartwig, J. F.; Zhao, H. ACS Catal. 2013, 3, 2856. doi: 10.1021/cs400633a
	(c) Du, Z.-T.; Shao, Z.-H. Chem. Soc. Rev. 2013, 42, 1337. doi: 10.1039/C2CS35258C
	(d) Pellissier, H. Adv. Synth. Catal. 2020, 362, 2289. doi: 10.1002/adsc.202000210
	(e) Chakraborty, N.; Das, B.; Rajbongshi, K. K.; Patel, B. K. Eur. J. Org. Chem. 2022, 2022, e202200273.
[2]	Zhou, J. Multicatalyst System in Asymmetric Catalysis, John Wiley & Sons, New York, 2014.
[3]	(a) Bredig, G.; Fiske, P. S. Biochem. Z. 1912, 46, 7.
	(b) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417. doi: 10.1021/ja00392a029
[4]	(a) Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1966, 7, 5239. doi: 10.1016/S0040-4039(01)89263-7
	(b) Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2024.
	(c) Noyori, R. Angew. Chem. Int. Ed. 2002, 41, 2008.
	(d) Knowles, W. S. Angew. Chem. Int. Ed. 2002, 41, 1998.
[5]	(a) Chen, K. Q.; Arnold, F. H. Proc. Natl. Acad. Sci. 1993, 90, 5618. doi: 10.1073/pnas.90.12.5618
	(b) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, VCH, Weinheim, 1995.
	(c) Voss, C. V.; Gruber, C. C.; Kroutil, W. Angew. Chem. Int. Ed. 2008, 120, 753. doi: 10.1002/ange.200703296
	(d) Marchetti, L.; Levine, M. ACS Catal. 2011, 1, 1090. doi: 10.1021/cs200171u
[6]	(a) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. doi: 10.1021/ja994280y
	(b) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. doi: 10.1021/ja000092s
	(c) List. B. Chem. Rev. 2007, 107, 5413. doi: 10.1021/cr078412e
	(d) MacMillan. D. W. C. Nature 2008, 455, 304. doi: 10.1038/nature07367
[7]	Peng, Y.-B.; Huo, X.-H.; Luo, Y.-C.; Wu, L.; Zhang, W.-B. Angew. Chem. Int. Ed. 2021, 60, 24941. doi: 10.1002/anie.202111842
[8]	For reviews: (a) Zhong, C.; Shi, X.-D. Eur. J. Org. Chem. 2010, 2999.
	(b) Allen, A. E.; MacMillan, D. W. C. Chem. Sci. 2012, 3, 633. doi: 10.1039/c2sc00907b
	(c) Borah, B.; Dwivedi, K. D.; Chowhan, L. R. Asian J. Org. Chem. 2021, 10, 2709. doi: 10.1002/ajoc.202100427
[9]	(a) Long, J.; Ding, K.-L. Angew. Chem. Int. Ed. 2001, 40, 544.
	(b) Zhou, J.; Wakchaure, V.; Kraft, P.; List, B. Angew. Chem. Int. Ed. 2008, 47, 7656. doi: 10.1002/anie.200802497
	(c) Lv, J.; Li, X.; Zhong, L.; Luo, S.-Z; Cheng, J.-P. Org. Lett. 2010, 12, 1096. doi: 10.1021/ol1000928
	(d) Lv, J.; Zhang, L.; Zhou, Y.-M; Nie, Z.-X; Luo, S.-Z; Cheng, J.-P. Angew. Chem. Int. Ed. 2011, 50, 6610. doi: 10.1002/anie.201101254
	(e) 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. doi: 10.1021/jacs.5b11476
	(f) Zeng, X.-P.; Zhou, J. J. Am. Chem. Soc. 2016, 138, 8730. doi: 10.1021/jacs.6b05601
	(g) Gao, X.-T.; Gan, C.-C.; Liu, S.-Y.; Zhou, F.; Wu, H.-H.; Zhou, J. ACS Catal. 2017, 7, 8588. doi: 10.1021/acscatal.7b03370
	(h) Wu, W.-B.; Yu, X.; Yu, J.-S.; Wang, X.; Wang, W.-G.; Zhou, J. CCS Chem. 2021, 3, 2168.
	(i) Zhang, Z.; Zhang, Z.-H.; Zhou, F.; Zhou, J. Org. Lett. 2021, 23, 2726. doi: 10.1021/acs.orglett.1c00632
[10]	(a) Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222. doi: 10.1021/ar700133y pmid: 29676895
	For selected examples: (b) Longmire, J.; Wang, B.; Zhang, X.-M. J. Am. Chem. Soc. 2002, 124, 13400. pmid: 29676895
	(c) Yan, X.-X.; Peng, Q.; Zhang, Y.; Zhang, K.; Hong, W.; Hou, X.-L.; Wu, Y.-D. Angew. Chem. Int. Ed. 2006, 45, 1979. doi: 10.1002/anie.200503672 pmid: 29676895
	(d) Yan, X.-X.; Peng, Q.; Li, Q.; Zhang, K.; Yao, J.; Hou, X.-L.; Wu, Y.-D. J. Am. Chem. Soc. 2008, 130, 14362. doi: 10.1021/ja804527r pmid: 29676895
	(e) Xu, H.; Zuend, S. J.; Woll, M. J.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986. doi: 10.1126/science.1182826 pmid: 29676895
	(f) Beletskaya, I. P.; Nájera, C.; Yus, M. Chem. Rev. 2018, 118, 5080. doi: 10.1021/acs.chemrev.7b00561 pmid: 29676895
[11]	(a) Shao, Z.-H.; Zhang, H. B. Chem. Soc. Rev. 2009, 38, 2745. doi: 10.1039/b901258n
	(b) Chen, D.-F.; Han, Z.-Y.; Zhou, X.-L.; Gong, L.-Z. Acc. Chem. Res. 2014, 47, 2365. doi: 10.1021/ar500101a
[12]	(a) Chen, G.-S.; Deng, Y.-J.; Gong, L.-Z.; Mi, A.-Q.; Cui, X.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567. pmid: 11594826
	(b) Nakoji, M.; Kanayama, T.; Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 3329. pmid: 11594826
[13]	(a) Ibrahem, I.; Córdova, A. Angew. Chem. Int. Ed. 2006, 45, 1952. doi: 10.1002/anie.200504021 pmid: 18772399
	(b) Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77. doi: 10.1126/science.1161976 pmid: 18772399
	(c) Yang, T.; Ferrali, A.; Sladojevich, F.; Campbell, L.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 9140. doi: 10.1021/ja9004859 pmid: 18772399
	(d) Li, B.-L; Liu, R.-R.; Liang, R.-X.; Jia, Y.-X. Acta Chim. Sinica 2017, 75, 448. (in Chinese). doi: 10.6023/A17020080 pmid: 18772399
	(李保乐, 刘人荣, 梁仁校, 贾义霞, 化学学报, 2017, 75, 448.) doi: 10.6023/A17020080 pmid: 18772399
	(e) Nair, V. V.; Arunprasath, D.; Pandidurai, S.; Sekar, G. Eur. J. Org. Chem. 2022, 2022, e202200244. pmid: 18772399
	(g) Nielsen, C. D.-T.; Linfoot, J. D.; Williamsa, A. F.; Spivey, A. C. Org. Biomol. Chem. 2022, 20, 2764. doi: 10.1039/D2OB00025C pmid: 18772399
[14]	(a) Klussmann, M. Angew. Chem. Int. Ed. 2009, 48, 7124. doi: 10.1002/anie.200903765 pmid: 19718737
	(b) Ren, L.; Lei, T.; Ye, J.-X.; Gong, L.-Z. Angew. Chem., nt. Ed. 2012, 51, 771. pmid: 19718737
	(c) Wu, X.; Li, M.-L.; Gong, L.-Z. Acta Chim. Sinica 2013, 71, 1091. (in Chinese). doi: 10.6023/A13030279 pmid: 19718737
	(吴祥, 李明丽, 龚流柱, 化学学报, 2013, 71, 1091.) doi: 10.6023/A13030279 pmid: 19718737
	(d) Yang, Z.-P.; Zhang, W.; You, S.-L. J. Org. Chem. 2014, 79, 7785. doi: 10.1021/jo501300k pmid: 19718737
	(e) Fang, G.-C.; Cheng, Y.-F.; Yu, Z.-L.; Li, Z.-L.; Liu, X.-Y. Top. in Current Chemistry 2019, 23. pmid: 19718737
[15]	(a) Lebeuf, R. I.; Hirano, K.; Glorius, F. Org. Lett. 2008, 10, 4243. doi: 10.1021/ol801644f pmid: 29377683
	(b) Cardinal-David, B.; Raup, D. E. A.; Scheidt, K. A. J. Am. Chem. Soc. 2010, 132, 5345. doi: 10.1021/ja910666n pmid: 29377683
	(c) Raup, D. E. A.; Cardinal-David, B.; Holte, D.; Scheidt, K. A. Nat. Chem. 2010, 2, 766. doi: 10.1038/nchem.727 pmid: 29377683
	(d) DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094. doi: 10.1021/ja3030164 pmid: 29377683
	(e) Wang, A.; Xiao, Y.-L.; Zhou, Y.; Xu, J.-Y.; Liu, H. Chin. J. Org. Chem. 2017, 37, 2590. (in Chinese). pmid: 29377683
	(王翱, 肖永龙, 周宇, 徐进宜, 柳红, 有机化学, 2017, 37, 2590.) doi: 10.6023/cjoc201702041 pmid: 29377683
	(f) Song, J.; Zhang, Z.-J.; Chen, S.-S.; Fan, T.; Gong, L.-Z. J. Am. Chem. Soc. 2018, 140, 3177. doi: 10.1021/jacs.7b12628 pmid: 29377683
	(g) Zhang, B.; Yang, G.-M.; Guo, D.-H.; Wang, J. Org. Chem. Front. 2022, 9, 5016. doi: 10.1039/D2QO00721E pmid: 29377683
[16]	(a) Arndtsen, B. A.; Gong L.-Z. Asymmetric Organocatalysis Combined with Metal Catalysis, Springer, Berlin, 2020.
	(b) Gong, L.-Z. Asymmetric Organo-Metal Catalysis: Concepts, Principles, and Applications, Wiley-VCH: Weinheim, 2021.
	(c) Zhang, M.-M.; Luo, Y.-Y.; Lu, L.-Q.; Xiao, W.-J. Acta Chim. Sinica 2018, 76, 838. (in Chinese). doi: 10.6023/A18060237
	(张毛毛, 骆元元, 陆良秋, 肖文精, 化学学报, 2018, 76, 838.) doi: 10.6023/A18060237
	(d) Tian, F.; Zhang, J.; Yang, W.-L.; Deng, W.-P. Chin. J. Org. Chem. 2020, 40, 3262. (in Chinese). doi: 10.6023/cjoc202005008
	(田飞, 张键, 杨武林, 邓卫平, 有机化学, 2020, 40, 3262.) doi: 10.6023/cjoc202005008
	(e) Bao, M.; Zhou, S.; Hu, W.-H.; Xu, X.-F. Chin. Chem. Lett. 2022, 33, 4969. doi: 10.1016/j.cclet.2022.04.050
	(f) Del Vecchio, A.; Sinibaldi, A.; Nori, V.; Giorgianni, G.; Di Carmine, G.; Pesciaioli, F. Chem. Eur. J. 2022, DOI: 10.1002/chem.202200818. doi: 10.1002/chem.202200818
[17]	(a) Xu, X.-F.; Zhou, J.; Yang, L.-P.; Hu, W.-H. Chem. Commun. 2008, 6564.
	(b) Hu, W.-H.; Xu, X.-F.; Zhou, J.; Liu, W.-J.; Huang, H.-X.; Hu, J.; Yang, L.-P.; Gong, L.-Z. J. Am. Chem. Soc. 2008, 130, 7782. doi: 10.1021/ja801755z
	(c) Qiu, H.; Li, M.; Jiang, L.-Q.; Lv, F.-P.; Zan, L.; Zhai, C.-W.; Doyle, M. P.; Hu, W.-H. Nat. Chem. 2012, 4, 733. doi: 10.1038/nchem.1406
[18]	Cai, Q.; Zhao, Z.-A.; You, S.-L. Angew. Chem. Int. Ed. 2009, 48, 7428. doi: 10.1002/anie.200903462
[19]	(a) Han, Z.-Y.; Xiao, H.; Chen, X.-H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 9182. doi: 10.1021/ja903547q
	(b) Liu, X.-Y.; Che, C.-M. Org. Lett. 2009, 11, 4204. doi: 10.1021/ol901443b
[20]	Yin, X.-P.; Zeng, X.-P.; Liu, Y.-L.; Liao, F.-M.; Yu, J.-S.; Zhou, F.; Zhou, J. Angew. Chem. Int. Ed. 2014, 53, 13740. doi: 10.1002/anie.201407677
[21]	Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471. pmid: 18072803
[22]	Erkkilä, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416. doi: 10.1021/cr068388p
[23]	(a) Schwemberger, W.; Gordon, W.; Chem. Zentralbl. 1935, 106, 514.
	(b) Gassman, P. G.; Meyer, G.; Williams, F. J. J. Am. Chem. Soc. 1972, 94, 7741. doi: 10.1021/ja00777a602
	(c) Norman, R. O. C.; Parr, W. J. E.; Thomas, C. B. J. Chem. Soc. Perkin Trans. 1 1976, 1983.
	(d) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285.
[24]	Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415.
[25]	Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395. doi: 10.1038/nature05592
[26]	(a) Hashmi, A. S. K.; Rudolph, M. Chem. Soc. Rev. 2008, 37, 1766. doi: 10.1039/b615629k pmid: 26673389
	(b) Alcaide, B.; Almendros, P.; Alonso, J. M. Molecules 2011, 16, 7815. doi: 10.3390/molecules16097815 pmid: 26673389
	(c) Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448. doi: 10.1039/C1CS15279C pmid: 26673389
	(d) Barbour, P. M.; Marholz, L. J.; Chang, L.; Xu, W.; Wang, X. Chem. Lett. 2014, 43, 572. doi: 10.1246/cl.131230 pmid: 26673389
	(e) Fensterbank, L.; Malacria, M. Acc. Chem. Res. 2014, 47, 953. doi: 10.1021/ar4002334 pmid: 26673389
	(f) Füerstner, A. Angew. Chem., Int. Ed. 2014, 53, 8587. doi: 10.1002/anie.201402719 pmid: 26673389
	(g) Füerstner, A. Acc. Chem. Res. 2014, 47, 925. doi: 10.1021/ar4001789 pmid: 26673389
	(h) Zhang, Y.; Luo, T.; Yang, Z. Nat. Prod. Rep. 2014, 31, 489. doi: 10.1039/c3np70075e pmid: 26673389
	(i) Pflästerer, D.; Hashmi, A. S. K. Chem. Soc. Rev. 2016, 45, 1331. doi: 10.1039/c5cs00721f pmid: 26673389
[27]	Early review of organo/Au cooperative catalysis: (a) Loh, C. C. J.; Ender, D. Chem. Eur. J. 2012, 18, 10212. doi: 10.1002/chem.201200287
	Recent review of chiral organo/Au cooperative catalysis for alkyne functionalization: (b) Bao, M.; Zhou, S.; Hu, W.-H.; Xu, X.-F. Chin. Chem. Lett. 2022, 33, 4969. doi: 10.1016/j.cclet.2022.04.050
[28]	(a) Zhou, J. Chem. Asian J. 2010, 5, 422. doi: 10.1002/asia.200900458
	(b) Patil, N. T.; Shinde, V. S.; Gajula, B. Org. Biomol. Chem. 2012, 10, 211. doi: 10.1039/C1OB06432K
[29]	(a) Belot, S.; Vogt, K. A.; Besnard, C.; Krause, N.; Alexakis, A. Angew. Chem., Int. Ed. 2009, 121, 9085.
	(b) Khin, C.; Hashmi, A. S. K. Rominger, F. Eur. J. Inorg. Chem. 2010, 1063.
[30]	Zweifel, T.; Hollmann, D.; Prüger, B.; Nielsen, M.; Jørgensen. K. A. Tetrahedron: Asymmetry 2010, 21, 1624.
[31]	Wu, X.; Li, M.-L.; Chen, D. F.; Chen, S.-S. J. Org. Chem. 2014, 79, 4743. doi: 10.1021/jo5006729
[32]	Hack, D.; Loh, C. C. J.; Hartmann, J. M.; Raabe, G.; Enders, D. Chem. Eur. J. 2014, 20, 3917. doi: 10.1002/chem.201400407
[33]	Loh, C. C. J.; Badorrek, J.; Raabe, G.; Enders, D. Chem. Eur. J. 2011, 17, 13409. doi: 10.1002/chem.201102793
[34]	(a) Belot, S.; Vogt, K. A.; Besnard, C.; Krause, N.; Alexakis, A. Angew. Chem. Int. Ed. 2009, 48, 8923. doi: 10.1002/anie.200903905
	(b) Belot, S.; Quintard, A.; Krause, N.; Alexakis, A. Adv. Synth. Catal. 2010, 352, 667. doi: 10.1002/adsc.200900814
[35]	You, Z.-H.; Chen, Y.-H.; Wu, X.-N.; Liu, Y.-K. Adv. Synth. Catal. 2017, 359, 4260. doi: 10.1002/adsc.201701071
[36]	Chiarucci, M.; di Lillo, M.; Romaniello, A.; Cozzi, P. G.; Cera, G.; Bandini, M. Chem. Sci. 2012, 3, 2859. doi: 10.1039/c2sc20478a
[37]	Ballesteros, A.; Morán-Poladura, P.; González, J. M. Chem. Commun. 2016, 52, 2905. doi: 10.1039/C5CC09529H
[38]	Jensen, K. L.; Franke, P. T.; Arrniz, C.; Kobbelgaard, S.; Jørgensen, K. A. Chem. Eur. J. 2010, 16, 1750. doi: 10.1002/chem.200903405
[39]	Yu, C.-G.; Ji, P.; Zhang, Y.-T.; Meng, X.; Wang, W. Org. Lett. 2021, 23, 7656. doi: 10.1021/acs.orglett.1c02916
[40]	Genet, M.; Takfaoui, A.; Marrot, J.; Greck, C.; Moreau, X. Adv. Synth. Catal. 2021, 363, 4516. doi: 10.1002/adsc.202100756
[41]	Monge, D.; Jensen, K. L.; Franke, P. T.; Lykke, L.; Jørgensen, K. A. Chem. Eur. J. 2010, 16, 9478. doi: 10.1002/chem.201001123
[42]	Chen, X.-J.; Chen, H.; Ji, X.; Jiang, H.-L.; Yao, Z.-J.; Liu, H. Org. Lett. 2013, 15, 1846. doi: 10.1021/ol4004542
[43]	Barber, D. M.; Sanganee, H. J.; Dixon, D. J. Org. Lett. 2012, 14, 5290. doi: 10.1021/ol302459c pmid: 23039069
[44]	Barber, D. M.; Ďuriš, A.; Thompson, A. L.; Sanganee, H. J.; Dixon, D. J. ACS Catal. 2014, 4, 634. pmid: 24563809
[45]	Urban, M.; Nigríni, M.; Císařová, I.; Veselý, J. J. Org. Chem. 2021, 86, 18139. doi: 10.1021/acs.joc.1c02428
[46]	Guo, W.-G.; Li, L.; Ding, Q.; Lin, X.-F.; Liu, X.-H.; Wang, K.; Liu, Y.; Fan, H.-J.; Li, C. ACS Catal. 2018, 8, 10180. doi: 10.1021/acscatal.8b02157
[47]	(a) Saito, H.; Iwai, R.; Uchiyama, T.; Miyake, M.; Miyairi, S. Chem. Pharm. Bull. 2010, 58, 872. doi: 10.1248/cpb.58.872
	(b) Terada, M.; Toda, Y. Angew. Chem., nt. Ed. 2012, 51, 2093.
	(c) Guo, X.; Hu, W.-H. Acc. Chem. Res. 2013, 46, 2427. doi: 10.1021/ar300340k
	(d) Chen, D.-F.; Wu, P.-Y.; Gong, L.-Z. Org. Lett. 2013, 15, 3958. doi: 10.1021/ol4017386
	(e) Meng, X.-L.; Yang, B.-M.; Zhang, L.-X.; Pan, G.-Y.; Zhang, X.-H.; Shao, Z.-H. Org. Lett. 2019, 21, 1292. doi: 10.1021/acs.orglett.8b04051
[48]	Ho, T.-L. Chem. Rev. 1975, 75, 1. doi: 10.1021/cr60293a001
[49]	Fructos, M. R.; Beldrrain, T. R.; de Frémont, P.; Scott, N. M.; Nolan, S. P.; Díaz-Requejo, M. M.; Pérez, P. J. Angew. Chem., Int. Ed. 2005, 44, 5284. doi: 10.1002/anie.200501056
[50]	Briones, J. F.; Davies, H. M. L. J. Am. Chem. Soc. 2012, 134, 11916. doi: 10.1021/ja304506g pmid: 22770434
[51]	Cao, Z.-Y.; Zhao, Y.-L.; Zhou, J. Chem. Commun. 2016, 52, 2537. doi: 10.1039/C5CC10096H
[52]	Zhao, Y.-L.; Cao, Z.-Y.; Zeng, X.-P.; Shi, J.-M.; Yu, Y.-H.; Zhou, J. Chem. Commun. 2016, 52, 3943. doi: 10.1039/C6CC00333H
[53]	Liao, F.-M.; Du, Y.; Zhou, F.; Zhou, J. Acta Chim. Sinica 2018, 76, 862. (in Chinese). doi: 10.6023/A18060238
	(廖富民, 杜溢, 周锋, 周剑, 化学学报, 2018, 76, 862.) doi: 10.6023/A18060238
[54]	Liao, F.-M.; Cao, Z.-Y.; Yu, J.-S.; Zhou, J. Angew. Chem. Int. Ed. 2017, 56, 2459. doi: 10.1002/anie.201611625
[55]	Annaka, M.; Yasuda, K.; Yamada, M.; Kawai, A.; Takamura, N.; Sugasawa, S.; Matsuoka, Y.; Iwata, H.; Fukushima, T. Heterocycles 1994, 39, 251. doi: 10.3987/COM-94-S(B)20
[56]	Cui, X.-Y.; Zhao, Y.-L.; Chen, Y.-M.; Dong, S.-Z.; Zhou, F.; Wu, H. -H.; Zhou, J. Org. Lett. 2021, 23, 4864. doi: 10.1021/acs.orglett.1c01399
[57]	Dong, G.-Z.; Bao, M.; Xie, X.-D.; Jia, S.-K.; Hu, W.-H.; Xu, X.-F. Angew. Chem. Int. Ed. 2021, 60, 1992. doi: 10.1002/anie.202012678