Advances in Organocatalytic Asymmetric Reactions Involving Thioesters

doi:10.6023/A22100422

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (1): 64-83.DOI: 10.6023/A22100422 Previous Articles Next Articles

Review

硫酯参与的有机催化不对称反应研究进展

王晓晨^a, 季泽尧^a, 刘健^a, 王炳福^a^,^b, 金辉^a^,^*(), 张立新^a^,^*()

a 沈阳化工大学功能分子研究所硼镁资源开发与精细化工技术国家地方联合工程实验室沈阳 110142
b 辽宁科技大学化学工程学院鞍山 110031

投稿日期:2022-10-10 发布日期:2022-12-05

作者简介:

王晓晨, 1994年出生于山东菏泽, 2018年在山东第一医科大学获得学士学位, 2020年至今在张立新教授和金辉博士的指导下攻读硕士学位. 研究兴趣是发展以硫酯为底物的合成方法学合成具有潜在生物活性的分子.

季泽尧, 1998年出生于河南南阳, 2021年毕业于吉林化工学院制药工程专业获得学士学位. 2021年至今在张立新教授和金辉博士的指导下攻读硕士学位. 研究兴趣是发展新的合成方法学合成具有潜在生物活性的分子.

刘健, 1996年出生于辽宁鞍山, 2019年在辽宁科技大学获得学士学位. 2021年至今在张立新教授和金辉博士的指导下攻读硕士学位. 研究兴趣是发展新的合成方法学合成具有潜在生物活性的分子.

王炳福, 1992年出生于黑龙江哈尔滨, 2015年和2018年在辽宁科技大学先后获得学士和硕士学位, 2019年至今, 在张立新教授和金辉博士的指导下攻读博士学位. 研究方向为不对称有机小分子催化.

金辉讲师、硕士生导师. 1989年出生于辽宁丹东, 2011年在大连医科大学获得学士学位(药学). 2014年在沈阳药科大学获得硕士学位(药物化学). 2014年至2018年在韩国成均馆大学化学系学习并获得有机化学博士学位(导师：Do Hyun Ryu教授). 2018年加入沈阳化工大学功能分子研究所从事科研教学工作. 研究兴趣主要是发展新的合成方法学合成具有潜在生物活性的分子.

张立新教授、博士生导师. 1966年出生于辽宁锦州, 1987年在兰州大学获得学士学位. 1993年在沈阳化工研究院获得硕士学位. 2000年至2004年在英国利兹大学化学系学习并获得有机化学博士学位(导师：Ronald Grigg教授). 曾就职于沈阳化工研究院(1987~2000, 高级工程师)、2016年加入沈阳化工大学, 组建功能分子研究所. 研究兴趣主要是新农药、医药创制和有机合成方法学.

基金资助:
项目受辽宁省教育厅科学研究项目(LQ2020025); 南宁市科学研究与技术开发计划项目(20201043)

Advances in Organocatalytic Asymmetric Reactions Involving Thioesters

Xiaochen Wang^a, Zeyao Ji^a, Jian Liu^a, Bingfu Wang^a^,^b, Hui Jin^a(), Lixin Zhang^a()

a National-Local Joint Engineering Laboratory for Development of Boron and Magnesium Resources and Fine Chemical Technology and Institute of Functional Molecules, Shenyang University of Chemical Technology, Shenyang 110142
b School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 110031

Received:2022-10-10 Published:2022-12-05
Contact: ^*E-mail: hjin@syuct.edu.cn; zhanglixin@syuct.edu.cn
Supported by:
Science and Technology Project of Liaoning Education Department(LQ2020025); Nanning Scientific Research and Technology Development Program(20201043)

Thioesters play a very important role in biosynthesis and organic synthesis. Due to smaller orbital overlap of the C(2p) and S(3p) orbitals, the α-proton acidity of thioesters is higher than that of the related oxoesters, making thioesters useful enolate precursors in nature as well as in the laboratory. Meanwhile, thioesters are also efficient acylation reagents which can be used for the construction of ester bond and amide bond. Organocatalysis, a biomimetic catalysis usually with metal- free small organic molecules, is an emerging research field that has been booming since the beginning of the 21st century. In the past decade, many important achievements have been made in the organocatalytic asymmetric reactions involving thioester substrates, which have greatly broadened the reaction types of organocatalytic reactions with ester substrates and realized some reactions that cannot be achieved by using their oxoester analogues. The advances in organocatalytic asymmetric reactions involving thioesters are summarized in this review. According to the types of thioester substrates, these advances are classified to two types. One type is the organocatalytic asymmetric reactions with enolizable thioesters such as trifluoroethyl thioesters, malonic acid half-thioesters (MAHTs), monothiomalonates (MTMs) and dithiomalonates (DTMs). For these reactions, noncovalent interactions between catalysts and thioesters, including hydrogen bonding and ion pair interaction, have been used to promote the reaction and to achieve the high enantioselectivity. Another type is the catalytic asymmetric reactions with α,β-unsaturated thioesters. For the reaction of this type, various chiral organocatalysts, including chiral amines, ureas, NHC (N-heterocyclic carbene), isothiourea, amidine and others, not only activate the thioester substrates, but also control the enantioselectivity well through covalent and non-covalent bonds. Meanwhile, the mechanism of representative transformations will be briefly introduced and at last, the perspective in this area will be given.

Key words: thioesters, organocatalysis, asymmetric reaction, biomimetic synthesis

Cite this article

Xiaochen Wang, Zeyao Ji, Jian Liu, Bingfu Wang, Hui Jin, Lixin Zhang. Advances in Organocatalytic Asymmetric Reactions Involving Thioesters[J]. Acta Chimica Sinica, 2023, 81(1): 64-83.

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Fig. & Tab. 44

Figure 1. The reactivity characteristics of thioesters

序号	标题
1	引言
2	可烯醇化硫酯参与的不对称反应
2.1	多氟烷基取代硫酯参与的反应
2.2	α-羰基取代硫酯参与的反应
2.2.1	丙二酸半硫酯参与的反应
2.2.2	丙二酸单硫酯参与的反应
2.2.3	丙二酸二硫酯和β-酮硫酯参与的反应
2.2.4	α-氮取代乙酸硫酯参与的反应
3	α,β-不饱和硫酯参与的不对称反应
3.1	非共价催化α,β-不饱和硫酯的反应
3.2	共价催化α,β-不饱和硫酯的反应
4	总结与展望

Table 1. Organization of this review

Figure 2. Summary of organocatalytic asymmetric reactions involving thioesters

Figure 3. Enolizable thioesters

Figure 4. Michael addition reaction of trifluoroethyl thioester catalyzed by chiral amines

Figure 5. Michael addition reaction of α-CF3 substituted thioester catalyzed by chiral amines Michael addition reaction of α-CF3 substituted thioester catalyzed by chiral amines

Figure 6. Mannich reaction of α-aryl thioester catalyzed by tertiary amine-urea catalyst

Figure 7. MAHTs in the polyketide synthesis

Figure 8. Asymmetric Aldol reaction of MAHTs and aldehydes catalyzed by chiral sulfonamides

Figure 9. Asymmetric Aldol reaction of α-fluorinated MAHTs and aldehydes

Figure 10. Asymmetric Aldol reaction of fluorinated MAHT and isatins

Figure 11. Asymmetric Aldol reaction of MAHTs with trifluoromethyl ketones

Figure 12. Asymmetric Mannich reaction of MAHTs and imines catalyzed by Br?nsted base

Figure 13. Asymmetric Mannich reaction of MAHTs with imines catalyzed by chiral guanidine

Figure 14. Asymmetric Mannich reaction of isatin derived ketoimines with MAHT

Figure 15. Asymmetric decarboxylative Mannich reaction catalyzed by phosphine-containing zwitterion

Figure 16. Asymmetric decarboxylative Mannich reaction of N-cyanoimine with MAHT

Figure 17. Michael reaction of MAHTs with nitroolefins

Figure 18. Synthesis of δ-lactones via cascade reaction of MAHT with α,β-unsaturated aldehydes

Figure 19. Asymmetric reaction with MTMs

Figure 20. Asymmetric Michael addition of α-unsubstituted MTMs to nitroolefins

Figure 21. Asymmetric Michael addition of α-substituted MTMs to nitroolefins

Figure 22. Asymmetric Michael addition of α-substituted MTMs to nitroolefins for access to dihydrocoumarins

Figure 23. Asymmetric Michael reaction of α-fluorosubstituted MTM with nitroolefins

Figure 24. Biomimetic synthesis of 3,4-dihydrocoumarin spiro 3',4'-dihydropyranones

Figure 25. Asymmetric Mannich reactions of MTMs with imines or imine equivalents

Figure 26. Asymmetric Mannich reaction of α-fluorinated MTM with aldimine

Figure 27. Asymmetric Mannich reaction of α-substituted MTMs with isatin-derived ketimines

Figure 28. Asymmetric Mannich reaction of C-alkynyl N-Boc-N,O- acetal with MTM

Figure 29. Michael addition reaction of DTMs with α,β-unsaturated carbonyl compounds

Figure 30. Asymmetric Michael addition-lactonization reactions of β,γ-unsaturated-α-keto esters with DTM

Figure 31. Asymmetric Michael addition reactions of DTM with nitroolefins

Figure 32. Asymmetric Michael addition reaction of DTMs with β,β-disubstituted nitroolefins under “on water” conditions

Figure 33. Enantioselective Mannich reaction of aldimines with DTM or β-ketothioesters catalyzed by chiral phosphoric acids

Figure 34. Asymmetric Mannich reactions of DTM with imines or amidosulfones catalyzed by chiral squaramide

Figure 35. Asymmetric Michael addition reaction of α-alkylisocyano- thioacetates with vinyl ketones

Figure 36. Asymmetric Michael addition reaction of α-imino thioesters with enone

Figure 37. Asymmetric Michael addition reaction of thioacrylate with 1,3-dicarbonyl compounds

Figure 38. Asymmetric Michael addition-cyclization tandem reaction of α,β-unsaturated thioesters with acetylacetone

Figure 39. Aza-Michael cyclization of α,β-unsaturated thioesters catalyzed by chiral phosphoric acid

Figure 40. Covalent catalytic reactions with α,β-unsaturated thioesters

Figure 41. Asymmetric isomerization of ω-hydroxy-α,β-unsaturated thioesters catalyzed by a bifunctional aminothiourea catalyst

Figure 42. Reaction of the conversion of α,β-unsaturated thioesters to 3,4-unsubstituted chiral thiochromenes

Figure 43. Stereoselective tandem rearrangement of α,β-unsaturated thioesters

References 87

[1]	(a) Ding, K. L.; Fan, Q. H. Asymmetric Catalysis: New Concepts and Methods, Chemical Industry Press, Beijing, 2009. (in Chinese)
	( 丁奎岭, 范青华, 不对称催化新概念与新方法, 化学工业出版社, 北京, 2009.)
	(b) Ding, K. L. Acta Chim. Sinica 2014, 72, 755. (in Chinese) doi: 10.6023/A1407E001
	( 丁奎岭, 化学学报 2014, 72, 755.) doi: 10.6023/A1407E001
	(c) Dalko, P. I. Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications, Wiley-VCH Verlag GmbH, Weinheim, 2013.
[2]	Saha, D.; Kharbanda, A.; Yan, W.; Lakkaniga, N. R.; Frett, B.; Li, H.-y. J. Med. Chem. 2020, 63, 441. doi: 10.1021/acs.jmedchem.9b00640
[3]	(a) Mulholland, A. J.; Lyne, P. D.; Karplus, M. J. Am. Chem. Soc. 2000, 122, 534. doi: 10.1021/ja992874v pmid: 8011640
	(b) Usher, K. C.; Remington, S. J.; Martin, D. P.; Drueckhammer, D. G. Biochemistry 1994, 33, 7753. pmid: 8011640
	(c) Wiegand, G.; Remington, S. J. Ann. Rev. Biophys. Chem. 1986, 15, 97. pmid: 8011640
[4]	(a) Hill, A. M. Nat. Prod. Rep. 2006, 23, 256. doi: 10.1039/B301028G pmid: 11548049
	(b) Staunton, J.; Weissman, K. J. Nat. Prod. Rep. 2001, 18, 380. doi: 10.1039/a909079g pmid: 11548049
[5]	(a) Masamune, S.; Kamata, S.; Schilling, W. J. Am. Chem. Soc. 1975, 97, 3515. pmid: 893906
	(b) Masamune, S.; Hayase, Y.; Schilling, W.; Chan, W. K.; Bates, G. S. J. Am. Chem. Soc. 1977, 99, 6756. pmid: 893906
[6]	Yang, X.; Ma, Y.; Di, H.; Wang, X.; Jin, H.; Ryu, D. H.; Zhang, L. Adv. Synth. Catal. 2021, 363, 3201. doi: 10.1002/adsc.202100369
[7]	(a) Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189.
	(b) Miyazaki, T.; Han-ya, Y.; Tokuyama, H.; Fukuyama, T. Synlett 2004, 477.
	(c) Fukuyama, T.; Tokuyama, H. Aldrichimica Acta 2004, 37, 87.
	(d) Mori, Y.; Seki, M. Adv. Synth. Catal. 2007, 349, 2027. doi: 10.1002/adsc.200600610
	(e) Cherney, A. H.; Reisman, S. E. Tetrahedron 2014, 70, 3259. doi: 10.1016/j.tet.2013.11.104
[8]	Um, P.-J.; Drueckhammer, D. G. J. Am. Chem. Soc. 1998, 120, 5607.
[9]	(a) Hirschbeck, V.; Gehrtz, P. H.; Fleischer, I. Chem. Eur. J. 2018, 24, 7092. doi: 10.1002/chem.201705025
	(b) Ye, Q.; Cao, W.-G.; Gao, J.-S. Chin. J. Org. Chem. 2002, 21, 697. (in Chinese)
	( 叶青, 曹卫国, 高金森, 有机化学, 2002, 21, 697.)
[10]	(a) Magdziak, D.; Lalic, G.; Lee, M. H.; Fortner, K. C.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2005, 127, 7284. pmid: 15898756
	(b) Orlandi, S.; Benaglia, M.; Cozzi, F. Tetrahedron Lett. 2004, 45, 1747. pmid: 15898756
	(c) Sawa, M.; Miyazaki, S.; Yonesaki, R.; Morimoto, H.; Ohshima, T. Org. Lett. 2018, 20, 5393. doi: 10.1021/acs.orglett.8b02306 pmid: 15898756
	(d) Furutachi, M.; Mouri, S.; Matsunaga, S.; Shibasaki, M. Chem. Asian J. 2010, 5, 2351. doi: 10.1002/asia.201000540 pmid: 15898756
[11]	Walker, M. C.; Thuronyi, B. W.; Charkoudian, L. K.; Lowry, B.; Khosla, C.; Chang, M. C. Y. Science 2013, 341, 1089. doi: 10.1126/science.1242345 pmid: 24009388
[12]	(a) Xiang, S.-H.; Tan, B. Nat. Commun. 2020, 11, 3786. doi: 10.1038/s41467-020-17580-z
	(b) 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
	(c) Di, H.; Liu, Y.; Ma, Y.; Yang, X.; Jin, H.; Zhang, L. Chin. J. Org. Chem. 2021, 41, 2228. (in Chinese) doi: 10.6023/cjoc202010039
	( 底慧明, 刘云婷, 马艳榕, 杨鑫悦, 金辉, 张立新, 有机化学, 2021, 41, 2228.) doi: 10.6023/cjoc202010039
	(d) Ren, H.; Ma, M.; Huang, Y. Chin. J. Org. Chem. 2022, 42, 3129. (in Chinese) doi: 10.6023/cjoc202208024
	任红霞, 马萌萌, 黄有, 有机化学, 2022, 42, 3129.). doi: 10.6023/cjoc202208024
	(e) Chen, X.; Wang, H.; Jin, Z.; Chi, Y. R. Chin. J. Chem. 2020, 38, 1167. doi: 10.1002/cjoc.202000107
[13]	Bordwell, F. G.; Fried, H. E. J. Org. Chem. 1991, 56, 4218. doi: 10.1021/jo00013a027
[14]	Um, P.-J.; Drueckhammer, D. G. J. Am. Chem. Soc. 1998, 120, 5605. doi: 10.1021/ja980445b
[15]	Alonso, D. A.; Kitagaki, S.; Utsumi, N.; Barbas III, C. F. Angew. Chem., Int. Ed. 2008, 47, 4588. doi: 10.1002/anie.200801088 pmid: 18464230
[16]	Hayashi, Y.; Yamada, T.; Sato, M.; Watanabe, S.; Kwon, E.; Iwasaki, K.; Umemiya, S. Org. Lett. 2019, 21, 5183. doi: 10.1021/acs.orglett.9b01774 pmid: 31247799
[17]	Kohler, M. C.; Yost, J. M.; Garnsey, M. R.; Coltart, D. M. Org. Lett. 2010, 12, 3376. doi: 10.1021/ol101152b pmid: 20608684
[18]	Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed., Oxford University Press, New York, 2012, pp. 628-630.
[19]	Kobuke, Y.; Yoshida, J.-i. Tetrahedron Lett. 1978, 19, 367. doi: 10.1016/S0040-4039(01)85127-3
[20]	(a) Magdziak, D.; Lalic, G.; Lee, H. M.; Fortner, K. C.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2005, 127, 7284. pmid: 17263375
	(b) Fortner, K. C.; Shair, M. D. J. Am. Chem. Soc. 2007, 129, 1032. pmid: 17263375
	(c) Lalic, G.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2003, 125, 2852. doi: 10.1021/ja029452x pmid: 17263375
	(d) Orlandi, S.; Benaglia, M.; Cozzi, F. Tetrahedron Lett. 2004, 45, 1747. pmid: 17263375
[21]	Bae, H. Y.; Sim, J. H.; Lee, J.-W.; List, B.; Song, C. E. Angew. Chem., Int. Ed. 2013, 52, 12143. doi: 10.1002/anie.201306297
[22]	Wang, Y.; Huang, G.; Hu, S.; Jin, K.; Wu, Y.; Chen, F. Tetrahedron Lett. 2017, 73, 5055. doi: 10.1016/j.tet.2017.05.066
[23]	(a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. doi: 10.1126/science.1131943 pmid: 18197347
	(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 32. pmid: 18197347
	(c) O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308. doi: 10.1039/b711844a pmid: 18197347
[24]	Saadi, J.; Akakura, M.; Yamamoto, H. J. Am. Chem. Soc. 2011, 133, 14248. doi: 10.1021/ja2066169
[25]	Saadi, J.; Wennemers, H. Nat. Chem. 2016, 8, 276. doi: 10.1038/nchem.2437
[26]	Zetschok, D.; Heieck, L.; Wennemers, H. Org. Lett. 2021, 23, 1753. doi: 10.1021/acs.orglett.1c00172 pmid: 33591192
[27]	(a) Bao, Y.; Kumagai, N.; Shibasaki, M. Chem. Sci. 2015, 6, 6124. doi: 10.1039/C5SC02218E pmid: 19722664
	(b) Misaki, T.; Takimoto, G.; Sugimura, T. J. Am. Chem. Soc. 2010, 132, 6286. doi: 10.1021/ja101216x pmid: 19722664
	(c) Yamaguchi, A.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 10842. doi: 10.1021/ja904575e pmid: 19722664
	(d) Saito, S.; Kobayashi, S. J. Am. Chem. Soc. 2006, 128, 8704. doi: 10.1021/ja061221t pmid: 19722664
	(e) Suto, Y.; Tsuji, R.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 3757. doi: 10.1021/ol051423e pmid: 19722664
[28]	Park, J. H.; Sim, J. H.; Song, C. E. Org. Lett. 2019, 21, 4567. doi: 10.1021/acs.orglett.9b01469
[29]	Ricci, A.; Pettersen, D.; Bernardi, L.; Fini, F.; Fochi, F.; Herrera, R. P.; Sgarzania, V. Adv. Synth. Catal. 2007, 349, 1037. doi: 10.1002/adsc.200600536
[30]	Pan, Y. H.; Kee, C. W.; Jiang, Z. Y.; Ma, T.; Zhao, Y. J.; Yang, Y. Y.; Xue, H. S.; Tan, C. H. Chem. Eur. J. 2011, 17, 8363. doi: 10.1002/chem.201100687
[31]	Hara, N.; Nakamura, S.; Sano, M. Chem. Eur. J. 2012, 18, 9276. doi: 10.1002/chem.201200367
[32]	(a) Takashina, N.; Price, C. C. J. Am. Chem. Soc. 1962, 84, 489. doi: 10.1021/ja00862a034
	(b) Rauhut, M. M.; Currier, H. A.; Semsel, A. M.; Wystrach, V. P. J. Org. Chem. 1961, 26, 5138. doi: 10.1021/jo01070a087
	(c) Morita, K.-i.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815. doi: 10.1246/bcsj.41.2815
[33]	(a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535. doi: 10.1021/ar000253x
	(b) Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035. doi: 10.1002/adsc.200404087
	(c) Lu, X.; Du, Y.; Lu, C. Pure Appl. Chem. 2005, 77, 1985. doi: 10.1351/pac200577121985
	(d) Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140. doi: 10.1039/b717758e
	(e) Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102. doi: 10.1039/b816700c
	(f) Wei, Y.; Shi, M. Acc. Chem. Res. 2010, 43, 1005. doi: 10.1021/ar900271g
	(g) Marinetti, A.; Voituriez, A. Synlett 2010, 2010, 174. doi: 10.1055/s-0029-1219157
	(h) Lu, Y.; Wang, S.-X.; Han, X.; Zhong, F.; Wang, Y. Synlett 2011, 2011, 2766. doi: 10.1055/s-0031-1289538
	(i) Zhao, Q.-Y.; Lian, Z.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 1724. doi: 10.1039/C1CC15793K
	(j) Fan, Y. C.; Kwon, O. Chem. Commun. 2013, 49, 11588. doi: 10.1039/c3cc47368f
	(k) Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927. doi: 10.1039/C4CS00054D
	(l) Xiao, Y.; Sun, Z.; Guo, H.; Kwon, O. J. Org. Chem. 2014, 10, 2089.
	(m) Wang, T.; Han, X.; Zhong, F.; Yao, W.; Lu, Y. Acc. Chem. Res. 2016, 49, 1369. doi: 10.1021/acs.accounts.6b00163
	(n) Li, W.; Zhang, J. Chem. Soc. Rev. 2016, 45, 1657. doi: 10.1039/C5CS00469A
	(o) Ni, H.; Chan, W.-L.; Lu, Y. Chem. Rev. 2018, 118, 9344. doi: 10.1021/acs.chemrev.8b00261
	(p) Guo, H.; Fan, Y. C.; Sun, Z.; Wu, Y.; Kwon, O. Chem. Rev. 2018, 118, 10049. doi: 10.1021/acs.chemrev.8b00081
[34]	(a) White, D. A.; Baizer, M. M. Tetrahedron Lett. 1973, 14, 3597. doi: 10.1016/S0040-4039(01)86980-X pmid: 23339132
	(b) Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819. doi: 10.1021/ja00102a071 pmid: 23339132
	(c) Trost, B. M.; Li, C.-J. J. Am. Chem. Soc. 1994, 116, 3167. doi: 10.1021/ja00086a074 pmid: 23339132
	(d) Trost, B. M.; Dake, G. R. J. Org. Chem. 1997, 62, 5670. doi: 10.1021/jo970848e pmid: 23339132
	(e) Zhang, C.; Lu, X. Synlett 1995, 1995, 645. doi: 10.1055/s-1995-5042 pmid: 23339132
	(f) Chung, Y. K.; Fu, G. C. Angew. Chem., Int. Ed. 2009, 48, 2225. doi: 10.1002/anie.200805377 pmid: 23339132
	(g) Smith, S. W.; Fu, G. C. J. Am. Chem. Soc. 2009, 131, 14231. doi: 10.1021/ja9061823 pmid: 23339132
	(h) Sun, J.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 4568. doi: 10.1021/ja101251d pmid: 23339132
	(i) Lundgren, R. J.; Wilsily, A.; Marion, N.; Ma, C.; Chung, Y. K.; Fu, G. C. Angew. Chem., Int. Ed. 2013, 52, 2525. doi: 10.1002/anie.201208957 pmid: 23339132
	(j) Chen, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Org. Chem. 1998, 63, 5631. doi: 10.1021/jo9721756 pmid: 23339132
[35]	(a) Zhong, F.; Dou, X.; Han, X.; Yao, W.; Zhu, Q.; Meng, Y.; Lu, Y. Angew. Chem., Int. Ed. 2013, 52, 943. doi: 10.1002/anie.201208285
	(b) Wang, T.; Yao, W.; Zhong, F.; Pang, G. H.; Lu, Y. Angew. Chem., Int. Ed. 2014, 126, 3008. doi: 10.1002/ange.201307757
	(c) Wang, T.; Yu, Z.; Hoon, D. L.; Huang, K.-W.; Lan, Y.; Lu, Y. Chem. Sci. 2015, 6, 4912. doi: 10.1039/C5SC01614B
	(d) Wang, T.; Hoon, D. L.; Lu, Y. Chem. Commun. 2015, 51, 10186. doi: 10.1039/C5CC03289J
	(e) Huang, G.; Ren, X.; Jiang, C.; Wu, J.-H.; Gao, G.; Wang, T. Org. Chem. Front. 2019, 6, 2872. doi: 10.1039/C9QO00478E
[36]	Wang, X.; Fang, F.; Zhao, C.; Tian, S.-K. Tetrahedron Lett. 2008, 49, 6442. doi: 10.1016/j.tetlet.2008.08.092
[37]	(a) Wang, H.-Y.; Zhang, K.; Zheng, C.-W.; Chai, Z.; Cao, D.-D.; Zhang, J.-X.; Zhao, G. Angew. Chem., Int. Ed. 2015, 54, 1775. doi: 10.1002/anie.201409342
	(b) Lou, Y.-P.; Zheng, C.-W.; Pan, R.-M.; Jin, Q.-W.; Zhao, G.; Li, Z. Org. Lett. 2015, 17, 688. doi: 10.1021/ol503712m
	(c) Xu, L.; Wang, H.; Zheng, C.; Zhao, G. Adv. Synth. Catal. 2017, 359, 2942. doi: 10.1002/adsc.201700321
	(d) Pan, R.; Zhang, J.; Zheng, C.; Wang, H.; Cao, D.; Cao, W.; Zhao, G. Tetrahedron 2017, 73, 2349. doi: 10.1016/j.tet.2017.03.005
	(e) Ji, X.; Cao, W.-G.; Zhao, G. Tetrahedron 2017, 73, 5983. doi: 10.1016/j.tet.2017.08.031
	(f) Jin, Q.; Zheng, C.; Zhao, G.; Zou, G. Tetrahedron 2018, 74, 4134. doi: 10.1016/j.tet.2018.06.030
	(g) Wang, H.-Y.; Zheng, C.-W.; Chai, Z.; Zhang, J.-X.; Zhao, G. Nat. Commun. 2016, 7, 12720. doi: 10.1038/ncomms12720
[38]	Zhang, H.; Jiang, C.; Tan, J.-P.; Hu, H.-L.; Chen, Y.; Ren, X.; Zhang, H.-S.; Wang, T. ACS Catal. 2020, 10, 5698. doi: 10.1021/acscatal.0c01079
[39]	(a) Fleming, F. F. Nat. Prod. Rep. 1999, 16, 597. doi: 10.1039/a804370a
	(b) Miller, J. S.; Manson, J. L. Acc. Chem. Res. 2001, 34, 563. doi: 10.1021/ar0000354
	(c) Lindquist, B. A.; Furse, K. E.; Corcelli, S. A. Phys. Chem. 2009, 11, 8119.
[40]	(a) Laine, D.; Palovich, M.; McCleland, B.; Petitjean, E.; Delhom, I.; Xie, H.; Deng, J.; Lin, G.; Davis, R.; Jolit, A.; Nevins, N.; Zhao, B.; Villa, J.; Schneck, J.; McDevitt, P.; Midgett, R.; Kmett, C.; Umbrecht, S.; Peck, B.; Davis, A.-B.; Bettoun, D. ACS Med. Chem. Lett. 2011, 2, 142. doi: 10.1021/ml100212k pmid: 30423248
	(b) Raja, V.-P.-A.; Perumal, S.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett. 2011, 21, 3881. doi: 10.1016/j.bmcl.2011.05.032 pmid: 30423248
	(c) Casimiro-Garcia, A.; Trujillo, J.-I.; Vajdos, F.; Juba, B.; Banker, M.-E.; Aulabaugh, A.; Balbo, P.; Bauman, J.; Chrencik, J.; Coe, J.-W.; Czerwinski, R.; Dowty, M.; Knafels, J.-D.; Kwon, S.; Leung, L.; Liang, S.; Robinson, R.-P.; Telliez, J.-B.; Unwalla, R.; Yang, X.; Thorarensen, A. J. Med. Chem. 2018, 61, 10665. doi: 10.1021/acs.jmedchem.8b01308 pmid: 30423248
[41]	Oyamada, Y.; Inaba, K.; Sasamori, T.; Nakamura, S. Chem. Commun. 2022, 58, 2172. doi: 10.1039/D1CC07191B
[42]	Lubkoll, J.; Wennemers, H. Angew. Chem., Int. Ed. 2007, 46, 6841. doi: 10.1002/anie.200702187
[43]	Bae, H. Y.; Some, S.; Lee, J. H.; Kim, J.-Y.; Song, M. J.; Lee, S.; Zhang, Y. J.; Song, C. E. Adv. Synth. Catal. 2011, 353, 3196. doi: 10.1002/adsc.201100458
[44]	(a) Chiu, P.; Leung, L. T.; Ko, B. C. B. Nat. Prod. Rep. 2010, 27, 1066. doi: 10.1039/b906520m pmid: 18389141
	(b) Florence, G. J.; Gardnerb, N. M.; Paterson, I. Nat. Prod. Rep. 2008, 25, 342. doi: 10.1039/b705661n pmid: 18389141
	(c) Boucard, V.; Broustal, G.; Campagne, J. M. Eur. J. Org. Chem. 2007, 225. pmid: 18389141
	(d) Mondon, M.; Gesson, J.-P. Curr. Org. Synth. 2006, 3, 41. doi: 10.2174/157017906775473966 pmid: 18389141
[45]	Ren, Q.; Sun, S.; Huang, J.; Li, W.; Wu, M.; Guo, H.; Wang, J.: Chem. Commun. 2014, 50, 6137. doi: 10.1039/C4CC01736F
[46]	Clerici, P.; Wennemers, H. Org. Biomol. Chem. 2012, 10, 110. doi: 10.1039/c1ob06638b pmid: 22068641
[47]	Kolarovic, A.; Käslin, A.; Wennemers, H. Org. Lett. 2014, 16, 4236. doi: 10.1021/ol501936n pmid: 25100030
[48]	Ling, T.; Rivas, F. Tetrahedron 2016, 72, 6729. doi: 10.1016/j.tet.2016.09.002
[49]	(a) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. doi: 10.1002/(SICI)1521-3773(19980302)37:4【-逻辑与-】#x00026;lt;388::AID-ANIE388【-逻辑与-】#x00026;gt;3.0.CO;2-V
	(b) Quasdorf, K. W.; Overman, L. E. Nature 2014, 516, 181. doi: 10.1038/nature14007
	(c) Liu, Y.; Han, S. J.; Liu, W. B.; Stoltz, B. M. Acc. Chem. Res. 2015, 48, 740. doi: 10.1021/ar5004658
	(d) Li, C.; Ragab, S. S.; Liu, G.; Tang, W. Nat. Prod. Rep. 2020, 37, 276. doi: 10.1039/C9NP00039A
[50]	(a) Arakawa, Y.; Fritz, S. P.; Wennemers, H. J. Org. Chem. 2014, 79, 3937. doi: 10.1021/jo500403q
	(b) Musa, M. A.; Cooperwood, J. S.; Khan, M. O. F. Curr. Med. Chem. 2008, 15, 2664. doi: 10.2174/092986708786242877
	(c) Asai, F.; Iinuma, M.; Tanaka, T.; Takenaka, M.; Mizuno, M. Phytochemistry 1992, 31, 2487. doi: 10.1016/0031-9422(92)83306-J
[51]	Sridharan, V.; Suryavanshi, P. A.; Menéndez, J. C. Chem. Rev. 2011, 111, 7157. doi: 10.1021/cr100307m
[52]	Engl, O. D.; Fritz, S. P.; Käslin, A.; Wennemers, H. Org. Lett. 2014, 16, 5454. doi: 10.1021/ol502697s
[53]	Cosimi, E.; Saadi, J.; Wennemers, H. Org. Lett. 2016, 18, 6014. pmid: 27934387
[54]	(a) He, M.; Uc, G. J.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 15088. doi: 10.1021/ja066380r pmid: 22468232
	(b) Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. J. Am. Chem. Soc. 2010, 132, 8810. doi: 10.1021/ja103631u pmid: 22468232
	(c) Belmessieri, D.; Morrill, L. C.; Simal, C.; Slawin, A. M.; Smith, A. D. J. Am. Chem. Soc. 2011, 133, 2714. doi: 10.1021/ja109975c pmid: 22468232
	(d) Mahatthananchai, J.; Kaeobamrung, J.; Bode, J. W. ACS Catal. 2012, 2, 494. pmid: 22468232
	(e) Morrill, L. C.; Douglas, J.; Lebl, T.; Slawin, A. M.; Fox, D. J.; Smith, A. D. Chem. Sci. 2013, 4, 4146. doi: 10.1039/c3sc51791h pmid: 22468232
	(f) Yao, W.; Dou, X.; Lu, Y. J. Am. Chem. Soc. 2015, 137, 54. doi: 10.1021/ja5109358 pmid: 22468232
	(g) Young, C. M.; Stark, D. G.; West, T. H.; Taylor, J. E.; Smith, A. D. Angew. Chem., Int. Ed. 2016, 55, 14394. doi: 10.1002/anie.201608046 pmid: 22468232
	(h) 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. doi: 10.1021/acs.orglett.6b02558 pmid: 22468232
	(i) Xu, D.; Zhang, Y.; Ma, D. Tetrahedron Lett. 2010, 51, 3827. doi: 10.1016/j.tetlet.2010.05.077 pmid: 22468232
	(j) Sinha, D.; Perera, S.; Zhao, J. C. G. Chem. Eur. J. 2013, 19, 6976. doi: 10.1002/chem.201300168 pmid: 22468232
[55]	Jin, H.; Lee, J.; Shi, H.; Lee, J. Y.; Yoo, E. J.; Song, C. E.; Ryu, D. H. Org. Lett. 2018, 20, 1584. doi: 10.1021/acs.orglett.8b00331
[56]	Bahlinger, A.; Fritz, S. P.; Wennemers, H. Angew. Chem., Int. Ed. 2014, 53, 8779. doi: 10.1002/anie.201310532 pmid: 24644150
[57]	Cosimi, E.; Engl, O. D.; Wennemers, H. Angew. Chem., Int. Ed. 2016, 55, 13127. doi: 10.1002/anie.201607146 pmid: 27632946
[58]	(a) Mitsunuma, H.; Shibasaki, M.; Kanai, M. Angew. Chem., Int. Ed. 2012, 51, 5217. doi: 10.1002/anie.201201132 pmid: 20063336
	(b) Shimizu, Y.; Kanai, M.; Shibasaki, M. Angew. Chem., Int. Ed. 2010, 49, 1103. doi: 10.1002/anie.200906678 pmid: 20063336
	(c) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. doi: 10.1021/ja991714g pmid: 20063336
	(d) Lemieux, R. M.; Meyers, A. I. J. Am. Chem. Soc. 1998, 120, 5453. doi: 10.1021/ja9804159 pmid: 20063336
[59]	Liu, T.; Liu, W.; Shao, Z. J. Org. Chem. 2015, 80, 4950. doi: 10.1021/acs.joc.5b00302
[60]	Engl, D. O.; Fritz, S. P.; Wennemers, H. Angew. Chem., Int. Ed. 2015, 54, 8193. doi: 10.1002/anie.201502976
[61]	(a) Trost, B. M.; Chung, C. K.; Pinkerton, A. B. Angew. Chem., Int. Ed. 2004, 43, 4327. doi: 10.1002/anie.200460058 pmid: 16551097
	(b) Fleming, J. J.; Du Bois, J. J. Am. Chem. Soc. 2006, 128, 3926. pmid: 16551097
[62]	Wang, Y.; Mo, M.; Zhu, K.; Zheng, C.; Zhang, H.; Wang, W.; Shao, Z. Nat. Commun. 2015, 6, 8544. doi: 10.1038/ncomms9544
[63]	Ye, W.; Jiang, Z.; Zhao, Y.; Goh, S. L. M.; Leow, D.; Soh, Y.-T.; Tan, C.-H. Adv. Synth. Catal. 2007, 349, 2454. doi: 10.1002/adsc.200700326
[64]	Jiang, Z.; Yang, Y.; Pan, Y.; Zhao, Y.; Liu, H.; Tan, C.-H. Chem. Eur. J. 2009, 15, 4925. doi: 10.1002/chem.200802601
[65]	Xu, J.; Fu, X.; Low, R.; Goh, Y.-P.; Jiang, Z.; Tan, C.-H. Chem. Commun. 2008, 5526.
[66]	(a) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672. doi: 10.1021/ja036972z
	(b) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119. doi: 10.1021/ja044370p
[67]	Jin, H.; Kim, S. T.; Hwang, G.-S.; Ryu, D. H. J. Org. Chem. 2016, 81, 3263. doi: 10.1021/acs.joc.6b00218
[68]	(a) Sim, J. H.; Song, C. E. Angew. Chem., Int. Ed. 2017, 56, 1835. doi: 10.1002/anie.201611466 pmid: 34163692
	(b) Klijn, J. E.; Engberts, J. B. F. N. Nature 2005, 435, 746. doi: 10.1038/435746a pmid: 34163692
	(c) Jung, Y.; Marcus, R. A. J. Am. Chem. Soc. 2007, 129, 5492. doi: 10.1021/ja068120f pmid: 34163692
	(d) Guo, W.; Liu, X.; Liu, Y.; Li, C. ACS Catal. 2018, 8, 328. doi: 10.1021/acscatal.7b02118 pmid: 34163692
	(e) Kitanosono, T.; Kobayashi, S. Chem. Eur. J. 2020, 26, 9408. doi: 10.1002/chem.201905482 pmid: 34163692
	(f) Cortes-Clerget, M.; Yu, J.; Kincaid, J. R. I.; Walde, P.; Gallou, F.; Lipshutz, B. H. Chem. Sci. 2021, 12, 4237. doi: 10.1039/d0sc06000c pmid: 34163692
[69]	Sim, J. H.; Park, J. H.; Maity, P.; Song, C. E. Org. Lett. 2019, 21, 6715. doi: 10.1021/acs.orglett.9b02320
[70]	(a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566. doi: 10.1002/anie.200353240 pmid: 15113196
	(b) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356. pmid: 15113196
	(c) Wu, X.; Li, M.; Gong, L. Acta Chim. Sinica 2013, 71, 1091. (in Chinese) doi: 10.6023/A13030279 pmid: 15113196
	( 吴祥, 李明丽, 龚流柱, 化学学报 2013, 71, 1091.) doi: 10.6023/A13030279 pmid: 15113196
[71]	Hatano, M.; Moriyama, K.; Maki, T.; Ishihara, K. Angew. Chem., Int. Ed. 2010, 49, 3823. doi: 10.1002/anie.201000824
[72]	Song, J.; Shih, H.-W.; Deng, L. Org. Lett. 2007, 9, 603. pmid: 17256945
[73]	Bae, H. Y.; Kim, M. J.; Sim, J. H.; Song, C. E. Angew. Chem., Int. Ed. 2016, 55, 10825. doi: 10.1002/anie.201605167
[74]	Gulevich, A. V.; Zhdanko, A. G.; Orru, R. V. A.; Nenajgenko, V. G. Chem. Rev. 2010, 110, 5235. doi: 10.1021/cr900411f pmid: 20608735
[75]	Odriozola, A.; Oiarbide, M.; Palomo, C. Chem. Eur. J. 2017, 23, 12758. doi: 10.1002/chem.201703526
[76]	Oh, J.-S.; Lee, J.-W.; Ryu, T. H.; Lee, J. H.; Song, C. E. Org. Biomol. Chem. 2012, 10, 1052. doi: 10.1039/C1OB06629C
[77]	Yoshida, Y.; Kasuya, R.; Mino, T.; Sakamoto, M. Org. Biomol. Chem. 2021, 19, 6402. doi: 10.1039/D1OB00829C
[78]	(a) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974. doi: 10.1021/ja9729950 pmid: 23772965
	(b) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431. pmid: 23772965
	(c) Dong, X.-Q.; Fang, X.; Wang, C.-J. Org. Lett. 2011, 13, 4426. doi: 10.1021/ol201766k pmid: 23772965
	(d) Fang, X.; Li, J.; Wang, C.-J. Org. Lett. 2013, 15, 3448. doi: 10.1021/ol4015305 pmid: 23772965
[79]	Rigby, C. L.; Dixon, D. J. Chem. Commun. 2008, 39, 3798.
[80]	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. doi: 10.1021/acs.joc.9b03216 pmid: 32053380
[81]	Maddocks, C. J.; Ermanis, K.; Clarke, P. A. Org. Lett. 2020, 22, 8116. doi: 10.1021/acs.orglett.0c03090
[82]	Fukata, Y.; Okamura, T.; Asano, K.; Matsubara, S. Org. Lett. 2014, 16, 2184. doi: 10.1021/ol500637x
[83]	Ahlemeyer, N. A.; Birman, V. B. Org. Lett. 2016, 18, 3454. doi: 10.1021/acs.orglett.6b01639 pmid: 27384085
[84]	Ahlemeyer, N. A.; Streff, E. V.; Muthupandi, P.; Birman, V. B. Org. Lett. 2017, 19, 6486. doi: 10.1021/acs.orglett.7b03044 pmid: 29200308
[85]	Lu, H.; Zhang, J.-L.; Liu, J.-Y.; Li, H.-Y.; Xu, P.-F. ACS Catal. 2017, 7, 7797. doi: 10.1021/acscatal.7b02651
[86]	(a) Das, J. P.; Marek, I. Chem. Commun. 2011, 47, 4593. doi: 10.1039/c0cc05222a
	(b) Minko, Y.; Pasco, M.; Lercher, L.; Botoshansky, M.; Marek, I. Nature 2012, 490, 522. doi: 10.1038/nature11569
[87]	Giacalone, F.; Gruttaduria, M.; Agrigento, P.; Noto, R. Chem. Soc. Rev. 2012, 41, 2406. doi: 10.1039/C1CS15206H

硫酯参与的有机催化不对称反应研究进展

Advances in Organocatalytic Asymmetric Reactions Involving Thioesters

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