过渡金属催化的不对称氢酰化反应研究进展

doi:10.6023/cjoc202207036

摘要/Abstract

过渡金属催化醛和π-不饱和键的氢酰化反应具有原料来源广泛、价廉易得的优点, 且具有高的原子和步骤经济性, 为C—C键的构筑提供了一条经济而高效的途径. 因此, 近几十年来, 该反应受到了持续而广泛的关注. 此篇综述将对过渡金属催化的不对称氢酰化反应的研究进展进行总结, 详细阐述反应类型、不对称控制方法和反应机理等.

关键词: 过渡金属催化, 氢酰化反应, 不对称催化, 醛, 烯烃

Transition metal-catalyzed hydroacylation reaction of aldehydes with π-unsaturated compounds provides an economical and efficient method for the construction of C—C bonds, not only allowing readily available starting materials to be used as substrates, but also featuring high atom and step economy. Therefore, the reaction has received continuous and extensive attention during the past several decades. The advances on enantioselective transition metal-catalyzed hydroacylation reactions are summarized, focusing on reaction types, asymmetric strategies and reaction mechanisms.

Key words: transition metal catalysis, hydroacylation, asymmetric catalysis, aldehydes, alkenes

引用此文

王豪锐, 叶萌春. 过渡金属催化的不对称氢酰化反应研究进展[J]. 有机化学, 2022, 42(10): 3152-3166.

Haorui Wang, Mengchun Ye. Research Advance on Enantioselective Transition Metal-Catalyzed Hydroacylation Reactions[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3152-3166.

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图/表 43

图式1. 过渡金属催化的氢酰化反应

Scheme 1. Transition metal-catalyzed hydroacylations

图式2. 当量金属催化的4-戊烯醛的氢酰化反应

Scheme 2. Hydroacylation of 4-pentenal catalyzed by stoichiometric metals

图式3. 2-二取代-4-戊烯醛的不对称氢酰化反应

Scheme 3. Asymmetric hydroacylation of 2-disubstituted 4-pentenal

图式4. 4-取代-4-戊烯醛的不对称氢酰化反应

Scheme 4. Asymmetric hydroacylation of 4-substituted 4-pentenals

表1. 阳离子Rh催化4-戊烯醛的不对称氢酰化

Table 1. Asymmetric hydroacylation of 4-pentenal via cationic Rh catalyst

表2. Rh催化4-戊烯醛的去对称化氢酰化反应

Table 2. Rh-catalyzed desymmetric hydroacylation of 4-pentenals

图式5. Rh催化3-取-4-戊烯醛的动力学拆分氢酰化反应

Scheme 5. Rh-catalyzed asymmetric hydroacylation of 3-subs- tituted 4-pentenals via kinetic resolution

图式6. Rh催化4-戊烯醛的动力学拆分氢酰化反应

Scheme 6. Rh-catalyzed asymmetric hydroacylation of 4-pentenals via kinetic resolution

图式7. 4-戊烯醛的不对称氢酰化反应

Scheme 7. Asymmetric hydroacylation of 4-pentenals

图式8. Rh催化2,2-二取代-4-戊烯醛的异氢酰化反应

Scheme 8. Rh-catalyzed isohydroacylation of 2,2-disubstituted 4-pentenals

图式9. Co催化2,2-二取代-4-戊烯醛的氢酰化反应

Scheme 9. Co-catalyzed hydroacylation of 2,2-disubstituted 4- pentenals

图式10. 动态动力学拆分的氢酰化反应

Scheme 10. Dynamic kinetic-resolution hydroacylation

表3. 不对称氢酰化的动态动力学拆分的最优配体

Table 3. Enantioselective DKR hydroacylation

图式11. 4-联烯醛的氢酰化反应

Scheme 11. Dynamic kinetic-resolution hydroacylation

图式12. 3-戊烯醛的不对称氢酰化反应

Scheme 12. Asymmetric hydroacylation of 3-pentenals

表4. 4-戊炔醛的动力学拆分

Table 4. Kinetic resolution of 4-alkynals

图式13. 4-戊炔醛的平行动力学拆分

Scheme 13. Parallel kinetic resolution of 4-alkynals

图式14. 环己二酮的去对称化

Scheme 14. Desymmetrization of dioxocyclohexane

图式15. 烯基苯甲醛的氢酰化反应

Scheme 15. Hydroacylation of 2-vinyl benzaldehydes

图式16. Rh催化芳基醛与酮的不对称氢酰化反应

Scheme 16. Rh-catalyzed asymmetric hydroacylation of aromatic aldehydes with ketones

图式17. Co催化酮和烯烃的不对称氢酰化反应

Scheme 17. Co-catalyzed asymmetric hydroacylation of alkenes or ketones

图式18. Rh催化氢酰化反应

Scheme 18. Rh-catalyzed hydroacylation

图式19. 亚胺离子-过渡金属协同催化的氢酰化反应

Scheme 19. Hydroacylation via cooperative catalysis of iminium-ion and transition-metal

图式20. Rh催化1,1,2-三取代烯烃不对称氢酰化反应

Scheme 20. Rh-catalyzed asymmetric hydroacylation of 1,1,2- trisubstituted alkenes

图式21. Co催化1,1,2-三取代烯烃不对称氢酰化反应

Scheme 21. Co-catalyzed asymmetric hydroacylation of 1,1,2- trisubstituted alkenes

图式22. 邻(2-烷基乙烯基)苯甲醛的不对称氢酰化

Scheme 22. Asymmetric hydroacylation of o-(2-alkylvinyl)benzaldehydes

图式23. Ir催化芳基醛与酮的不对称氢酰化反应

Scheme 23. Ir-catalyzed asymmetric hydroacylation of aromatic aldehydes with ketones

图式24. Rh催化的氢酰化反应合成含氮六元环

Scheme 24. Rh-catalyzed hydroacylation for synthesis of nitrogen-containing six-membered ring

图式25. Rh催化邻烯丙基苯甲醛的不对称氢酰化

Scheme 25. Rh-catalyzed enantioselective hydroacylation of ortho-allylbenzaldehydes

图式26. Rh催化烯烃氢酰化构筑中环

Scheme 26. Rh-catalyzed hydroacylation for synthesis of medium-sized ring

图式27. Rh催化酮的氢酰化构筑中环

Scheme 27. Rh-catalyzed hydroacylation of ketones for synthesis of medium-sized ring

图式28. 金属和有机分子协同催化构筑中环

Scheme 28. Metal-organic cooperative catalysis for medium-ring synthesis

图式29. 水杨醛和降冰片烯的不对称氢酰化反应

Scheme 29. Asymmetric hydroacylation of salicylaldehydes with norbornadienes

图式30. 1,3-二取代联烯和β-硫代醛的不对称氢酰化

Scheme 30. Asymmetric hydroacylation of 1,3-disubstituted allenes with β-S-substituted aldehydes

图式31. 水杨醛和高烯丙基硫化物的不对称氢酰化反应

Scheme 31. Asymmetric hydroacylation of homoallylic salicylaldehydes with sulfides

图式32. 水杨醛和环丙烯的不对称氢酰化

Scheme 32. Asymmetric hydroacylation of salicylaldehydes with cyclopropenes

图式33. 水杨醛和环丁烯的不对称氢酰化反应

Scheme 33. Asymmetric hydroacylation of salicylaldenhydes with cyclobutenes

图式34. 己二烯的不对称氢酰化

Scheme 34. Asymmetric hydroacylation of hexadienes

图式35. 醛和丙烯酰胺的不对称氢酰化反应

Scheme 35. Asymmetric hydroacylation of acrylamides and aldehydes

图式36. 醛和酮酰胺的不对称氢酰化反应

Scheme 36. Asymmetric hydroacylation of ketoamides and aldehydes

图式37. 醛和酮酰胺的不对称氢酰化

Scheme 37. Asymmetric hydroacylation of ketoamides and aldehyde

图式38. 醛和1,6-烯炔的不对称氢酰化反应

Scheme 38. Asymmetric hydroacylation of 1,6-enynes and aldehydes

图式39. 醛和1,3-二烯的不对称氢酰化反应

Scheme 39. Asymmetric hydroacylation of 1,3-dienes and aldehydes

参考文献 55

[1]	(a) Gandeepan, P.; Müller, T.; Zell, D.; Cera, G.; Warratz, S.; Ackermann, L. Chem. Rev. 2019, 119, 4, 2192. doi: 10.1021/acs.chemrev.8b00507
	(b) Qiu, Y.; Zhu, C.; Stangier, M.; Struwe, J.; Ackermann, L. CCS Chem. 2020, 2, 1529.
	(c) Tong, H.-R.; Li, B.; Li, G.; He, G.; Chen, G. CCS Chem. 2021, 3, 1797. doi: 10.31635/ccschem.020.202000426
	(d) Li, J.-F.; Luan, Y.-X.; Ye, M. Sci. China Chem. 2021, 64, 1923. doi: 10.1007/s11426-021-1068-2
	(e) Tao, P.; Jia, Y. Sci. China Chem. 2016, 59, 1109. doi: 10.1007/s11426-016-0058-7
[2]	For selected examples on other types of couplings of π-unsaturated compounds with aldehydes, see: (a) Zheng, Y.-L.; Ye, M. Chin. J. Chem. 2020, 38, 489. doi: 10.1002/cjoc.201900543
	(b) Han, X.-W.; Zhang, T.; Yao, W.-W.; Chen, H.; Ye, M. CCS Chem. 2020, 2, 955.
	(c) Han, X.-W.; Zhang, T.; Zheng, Y.-L.; Yao, W.-W.; Li, J.-F.; Pu, Y.-G.; Ye, M.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2018, 57, 5068. doi: 10.1002/anie.201801817
	(d) Zheng, Y.-L.; Luan, Y.-X.; Ye, M. Synlett 2016, 27, 2401. doi: 10.1055/s-0036-1588879
[3]	For selected reviews about hydroaclytion: (a) Christmann, M. Angew. Chem., Int. Ed. 2005, 44, 2632. doi: 10.1002/anie.200500761
	(b) Jun, C.-H.; Jo, E.-A.; Park, J.-W. Eur. J. Org. Chem. 2007, 12, 1869.
	(c) Willis, M. C. Chem. Rev. 2010, 110, 725. doi: 10.1021/cr900096x
	(d) DiRocco, D. A.; Rovis, T. Angew. Chem., Int. Ed. 2011, 50, 7982. doi: 10.1002/anie.201102920
	(e) Carlos, G.-R.; Willis, M. C. Pure Appl. Chem., 2011, 83, 577. doi: 10.1351/PAC-CON-10-09-23
	(f) Leung, J. C.; Krische, M. J. Chem. Sci. 2012, 3, 2202. doi: 10.1039/c2sc20350b
	(g) Watsona, I. D. G.; Toste, F. D. Chem. Sci. 2012, 3, 2899. doi: 10.1039/c2sc20542d
	(h) Murphy, S. K.; Bruch, A.; Dong, V. M. Angew. Chem., Int. Ed. 2014, 53, 2455. doi: 10.1002/anie.201309987
	(i) Murphy, S. K.; Dong, V. M. Chem. Commun. 2014, 50, 13645. doi: 10.1039/C4CC02276A
	(j) Ghosh, A.; Johnson, K. F.; Vickerman, K. L.; Walker, J. A., Jr.; Stanley, L. M. Org. Chem. Front. 2016, 3, 639. doi: 10.1039/C6QO00023A
	(k) Kim, D.-S.; Park, W.-J.; Jun, C.-H. Chem. Rev. 2017, 117, 8977. doi: 10.1021/acs.chemrev.6b00554
	(l) Davison, R. T.; Kuker, E. L.; Dong, V. M. Acc. Chem. Res. 2021, 54, 1236. doi: 10.1021/acs.accounts.0c00771
[4]	Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 13, 1287. doi: 10.1016/S0040-4039(01)84569-X
[5]	James, B. R.; Young, C. G. J. Chem. Soc., Chem. Commun. 1983, 7, 59.
[6]	James, B. R.; Young, C. G. J. Organomet. Chem. 1985, 285, 321. doi: 10.1016/0022-328X(85)87377-0
[7]	Taura, Y.; Tanaka, M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1989, 30, 6349. doi: 10.1016/S0040-4039(01)93891-2
[8]	Taura, Y.; Tanaka, M.; Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1991, 47, 4879. doi: 10.1016/S0040-4020(01)80954-6
[9]	Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1992, 33, 6331. doi: 10.1016/S0040-4039(00)60966-8
[10]	Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. Tetrahedron 1994, 50, 4335. doi: 10.1016/S0040-4020(01)89370-4
[11]	Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 946.
[12]	Richard, W. B.; McMorran, D. A.; Bosnich, B. Chem. Commun. 1997, 589.
[13]	Wu, X.-M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1993, 34, 5927. doi: 10.1016/S0040-4039(00)73816-0
[14]	Tanaka, M.; Imai, M.; Fujio, M.; Sakamoto, E.; Takahashi, M.; Eto-Kato, Y.; Wu, X.-M.; Funakoshi, K.; Sakai, K.; Suemune, H. J. Org. Chem. 2000, 65, 5806. pmid: 10970327
[15]	Richard, W. B.; Bosnich, B. Organometallics. 1995, 14, 4343. doi: 10.1021/om00009a043
[16]	Fujio, M.; Tanaka, M.; Wu, X.-M.; Funakoshi, K.; Sakai, K.; Suemune, H. Chem. Lett. 1998, 881.
[17]	Imai, M.; Tanaka, M.; Suemune, H. Tetrahedron. 2001, 57, 1205. doi: 10.1016/S0040-4020(00)01107-8
[18]	Hoffman, T. J.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 10670. doi: 10.1002/anie.201104595
[19]	Park, J. W.; Kou, K. G. M.; Kim, D. K.; Dong, V. M. Chem. Sci. 2015, 6, 4479. doi: 10.1039/C5SC01553G
[20]	Kim, D. K.; Riedel, J.; Kim, R. S.; Dong, V. M. J. Am. Chem. Soc. 2017, 139, 10208. doi: 10.1021/jacs.7b05327
[21]	Chen, Z.; Aota, Y.; Nguyen, H. M. H.; Dong, V. M. Angew. Chem., Int. Ed. 2019, 131, 4753.
[22]	Oonishi, Y.; Hosotani, A.; Yokoe, T.; Sato, Y. Org. Lett. 2019, 21, 4120. doi: 10.1021/acs.orglett.9b01307
[23]	Liu, C.; Yuan, J.; Zhang, Z.; Gridnev, I. D.; Zhang, W. Angew. Chem., Int. Ed. 2021, 60, 8997. doi: 10.1002/anie.202017190
[24]	Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 10296. pmid: 12197729
[25]	Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 8078. pmid: 12837058
[26]	Wu, X.; Chen, Z.; Bai, Y.-B.; Dong, V. M. J. Am. Chem. Soc. 2016, 138, 12013. doi: 10.1021/jacs.6b06227
[27]	Kundu, K.; McCullagh, J. V.; Morehead, A. T., Jr. J. Am. Chem. Soc. 2005, 127, 16042. doi: 10.1021/ja0564416
[28]	Phan, D. H. T.; Kim, B.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 15608. doi: 10.1021/ja907711a
[29]	Yang, J.; Yoshikai, N. J. Am. Chem. Soc. 2014, 136, 16748. doi: 10.1021/ja509919x
[30]	Ghosh, A.; Stanley, L. M. Chem. Commun. 2014, 50, 2765. doi: 10.1039/C4CC00210E
[31]	Vickerman, K. L.; Stanley, L. M. Org. Lett. 2017, 19, 5054. doi: 10.1021/acs.orglett.7b02230 pmid: 28933168
[32]	Rastelli, E. J.; Truong, N. T.; Coltart, D. M. Org. Lett. 2016, 18, 5588. pmid: 27767317
[33]	Johnson, K. F.; Schneider, E. A.; Schumacher, B. P.; Ellern, A.; Scanlon, J. D.; Stanley, L. M. Chem. Eur. J. 2016, 22, 15619. doi: 10.1002/chem.201603880
[34]	Yang, J.; Rérat, A.; Lim, Y. J.; Gosmini, C.; Yoshikai, N. Angew. Chem., Int. Ed. 2017, 129, 2489.
[35]	Yuan, J.; Liu, C.; Chen, Y.; Zhang, Z.; Yan, D.; Zhang, W. Tetrahedron 2019, 75, 269. doi: 10.1016/j.tet.2018.11.057
[36]	Shirai, T.; Iwasaki, T.; Kanemoto, K.; Yamamoto, Y. Chem. Asian J. 2020, 15, 1858. doi: 10.1002/asia.202000386
[37]	Du, X. W.; Ghosh, A.; Stanley, L. M. Org. Lett. 2014, 16, 4036. doi: 10.1021/ol501869s
[38]	Johnson, K. F.; Schmidt, A. C.; Stanley, L. M. Org. Lett. 2015, 17, 4654. doi: 10.1021/acs.orglett.5b02559
[39]	Coulter, M. M.; Doman, P. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 6932. doi: 10.1021/ja901915u
[40]	Shen, Z.; Khan, H. A.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2916. doi: 10.1021/ja7109025
[41]	Shen, Z.; Dornan, P. K.; Khan, H. A.; Woo, T. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 1077. doi: 10.1021/ja806758m
[42]	Khan, H. A.; Kou, K. G. M.; Dong, V. M. Chem. Sci. 2011, 2, 407. doi: 10.1039/C0SC00469C
[43]	Beletskiy, E. V.; Sudheer, C.; Douglas, C. J. J. Org. Chem. 2012, 77, 5884. doi: 10.1021/jo300779q pmid: 22775578
[44]	Vora, K. P.; Lochow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257. doi: 10.1016/S0022-328X(00)94430-9
[45]	Stemmler, R. T.; Bolm, C. Adv. Synth. Catal. 2007, 349, 1185. doi: 10.1002/adsc.200600583
[46]	Osborne, J. D.; Randell-Sly, H. E.; Currie, G. S.; Cowley, A. R.; Willis, M. C. J. Am. Chem. Soc. 2008, 130, 17232. doi: 10.1021/ja8069133 pmid: 19053453
[47]	Coulter, M. M.; Kou, K. G. M.; Galligan, B.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16330. doi: 10.1021/ja107198e
[48]	Phan, D. H. T.; Kou, K. G. M.; Dong, V. M. J. Am. Chem. Soc. 2010, 132, 16354. doi: 10.1021/ja107738a
[49]	Goetzke, F. W.; Siderab, M.; Fletcher, S. P. Chem. Sci. 2022, 13, 236 doi: 10.1039/D1SC06035J
[50]	Inui, Y.; Tanaka, M.; Imai, M.; Tanaka, K.; Suemune, H. Chem. Pharm. Bull. 2009, 57, 1158. doi: 10.1248/cpb.57.1158
[51]	Shibata, Y.; Tanaka, K. J. Am. Chem. Soc. 2009, 131, 12552. doi: 10.1021/ja905908z pmid: 19685873
[52]	Kou, K. G. M.; Le, D. N.; Dong, V. M. J. Am. Chem. Soc. 2014, 136, 9471. doi: 10.1021/ja504296x
[53]	Kou, K. G. M.; Longobardi, L. E.; Dong, V. M. Adv. Synth. Catal. 2015, 357, 2233. doi: 10.1002/adsc.201500313
[54]	Whyte, A.; Bajohr, J.; Torelli, A.; Lautens, M. Angew. Chem., Int. Ed. 2020, 59, 16409. doi: 10.1002/anie.202006716
[55]	Parsutkar, M. M.; RajanBabu T. V. J. Am. Chem. Soc. 2021, 143, 12825. doi: 10.1021/jacs.1c06245 pmid: 34351138