Progress in Heterocycles-Based Asymmetric Vinylogous Mannich Reactions and Applications to the Synthesis of Alkaloids

doi:10.6023/cjoc201806005

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (9): 2215-2230.DOI: 10.6023/cjoc201806005 Previous Articles Next Articles

Special Issue: 合成科学

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基于杂环的不对称插烯Mannich反应及其在生物碱合成中的应用进展

叶剑良, 黄培强

福建省化学生物学重点实验室能源材料化学协同创新中心厦门大学化学化工学院化学系厦门 361005

收稿日期:2018-06-03 修回日期:2018-08-22 发布日期:2018-08-22
通讯作者: 黄培强 E-mail:pqhuang@xmu.edu.cn
基金资助:
国家重点研发计划（No.2017YFA0207302）、国家自然科学基金（Nos.21332007，21472153）、教育部长江学者和创新团队发展计划、中央高校基本科研业务费专项资金（Nos.20720170092，20720180024）和福建省自然科学基金（No.2017J01021）资助项目.

Progress in Heterocycles-Based Asymmetric Vinylogous Mannich Reactions and Applications to the Synthesis of Alkaloids

Ye Jianliang, Huang Peiqiang

Fujian Provincial Key Laboratory of Chemical Biology, Collaborative Innovation Center of Chemistry for Energy Materials(iChEM), Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005

Received:2018-06-03 Revised:2018-08-22 Published:2018-08-22
Contact: 10.6023/cjoc201806005 E-mail:pqhuang@xmu.edu.cn
Supported by:
Project supported by the National Key R&D Program of China (No. 2017YFA0207302), the National Natural Science Foundation of China (Nos. 21332007, 21472153), the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT) of Ministry of Education, the Chinese Universities Scientific Fund (Nos. 20720170092, 20720180024) and the Natural Science Foundation of Fujian Province of China (No. 2017J01021).

Heterocycles (α,β/β,γ-unsaturated-γ-lactones, α,β-unsaturated-γ-lactams)-based vinylogous Mannich reactions (VMR) constitute a class of effective C-C bond formation approach to install vicinal aminol-containing α,β-unsaturated-lactones and vicinal diamine-containing α,β-unsaturated-γ-lactams. Possessing multiple functionalities, the latters are versatile building blocks for the synthesis of O-heterocycles, N-heterocycles and the synthesis of alkaloids. The progresses of the asymmetric vinylogous Mannich reactions of silyloxy pyrroles and silyloxy furans from 2011 to mid-2018 are summarized. The methods are organized according to chiral auxiliary-induced asymmetric VMRs, asymmetric VMRs catalyzed by metal-chiral ligand complex or organocatalyst, and the applications of the aymmetric VMRs to the syntheses of complex alkaloids. Some limitations of the developed heterocycles-based VMRs are also briefly discussed.

Key words: vinylogous Mannich reaction, silyloxy pyrrole, silyloxy furan, imine, chiral auxiliary, asymmetric catalysis, alkaloid, asymmetric total synthesis

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Ye Jianliang, Huang Peiqiang. Progress in Heterocycles-Based Asymmetric Vinylogous Mannich Reactions and Applications to the Synthesis of Alkaloids[J]. Chin. J. Org. Chem., 2018, 38(9): 2215-2230.

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[1] Liu, Y.; Wu, Q.; Yin, D.; Li, D. Chin. J. Org. Chem. 2016, 36, 927(in Chinese). (刘玉婷, 吴倩倩, 尹大伟, 李荻扬, 有机化学, 2016, 36, 927.)
[2] (a) Wehlauch, R.; Gademann, K. Asian J. Org. Chem. 2017, 6, 1146.
(b) Martin, S. F. Adv. Heterocycl. Chem. 2013, 110, 73.
[3] (a) Zhang, Q.; Liu, X.; Feng, X. Curr. Org. Synth. 2013, 10, 764.
(b) Casiraghi, G.; Battistini, L.; Curti, C.; Rassu, G.; Zanardi, F. Chem. Rev. 2011, 111, 3076.
(c) Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G. Synlett 2009, 1525.
(d) Martin, S. F. Acc. Chem. Res. 2002, 35, 895.
(e) Bur, S. K.; Martin, S. F. Tetrahedron 2001, 57, 3221.
[4] Sartori, A.; Dell'Amico, L.; Curti, C.; Battistini, L.; Pelosi, G.; Rassu, G.; Casiraghi, G.; Zanardi, F. Adv. Synth. Catal. 2011, 353, 3278.
[5] Sartori, A.; Dell'Amico, L.; Battistini, L.; Curti, C.; Rivara, S.; Pala, D.; Kerry, P. S.; Pelosi, G.; Casiraghi, G.; Rassu, G.; Zanardi, F. Org. Biomol. Chem. 2014, 12, 1561.
[6] Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600.
[7] Ruan, S.-T.; Luo, J.-M.; Du, Y.; Huang, P.-Q. Org. Lett. 2011, 13, 4938.
[8] Bur, S. K.; Martin, S. F. Org. Lett. 2000, 2, 3445.
[9] Harding, K. E.; Southard, J. M. Tetrahedron:Asymmetry 2005, 16, 1845.
[10] Guo, L.-D.; Liang, P.; Zheng, J.-F.; Huang, P.-Q. Eur. J. Org. Chem. 2013, 2230.
[11] Liu, R.-C.; Wei, J.-H.; Wei, B.-G.; Lin, G.-Q. Tetrahedron:Asymmetry 2008, 19, 2731.
[12] Altenbach, H.-J.; Himmeldirk, K. Tetrahedron:Asymmetry 1995, 6, 1077.
[13] Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachi, I.; Takahata, H. Tetrahedron:Asymmetry 2001, 12, 817.
[14] Nadin, A.; Sánchez López, J. M.; Neduvelil, J. G.; Thomas, S. R. Tetrahedron 2001, 57, 1861.
[15] Rao, V. U. B.; Jadhav, A. P.; Garad, D.; Singh, R. P. Org. Lett. 2014, 16, 648.
[16] Shi, Y.-H.; Wang, Z.; Shi, Y.; Deng, W.-P. Tetrahedron 2012, 68, 3649.
[17] Liu, L.-J.; Chen, L.-J.; Li, P.; Li, X.-B.; Liu, J.-T. J. Org. Chem. 2011, 76, 4675.
[18] Liu, L.-J.; Liu, J.-T. Tetrahedron 2014, 70, 1236.
[19] Yu, J.; Miao, Z.; Chen, R. Org. Biomol. Chem. 2011, 9, 1756.
[20] Tamura, O.; Takeda, K.; Mita, N.; Sakamoto, M.; Okamoto, I.; Morita, N.; Ishibashi, H. Org. Biomol. Chem. 2011, 9, 7411.
[21] Degiorgis, F.; Lombardo, M.; Trombini, C. Tetrahedron 1997, 53, 11721.
[22] Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772.
[23] Yuan, Z.-L.; Jiang, J.-J.; Shi, M. Tetrahedron 2009, 65, 6001.
[24] Zhao, Q.-Y.; Yuan, Z.-L.; Shi, M. Tetrahedron:Asymmetry 2010, 21, 943.
[25] Zhao, Q.-Y.; Yuan, Z.-L.; Shi, M. Adv. Synth. Catal. 2011, 353, 637.
[26] Zheng, L.-S.; Li, L.; Yang, K.-F.; Zheng, Z.-J.; Xiao, X.-Q.; Xu, L.-W. Tetrahedron 2013, 69, 8777.
[27] Hayashi, M.; Sano, M.; Funahashi, Y.; Nakamura, S. Angew. Chem., Int. Ed. 2013, 52, 5557.
[28] (a) Carswell, E. L.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2006, 45, 7230.
(b) Mandai, H.; Mandai, K.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2008, 130, 17961.
(c) Wieland, L. C.; Vieira, E. M.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 570.
[29] Curti, C.; Battistini, L.; Ranieri, B.; Pelosi, G.; Rassu, G.; Casiraghi, G.; Zanardi, F. J. Org. Chem. 2011, 76, 2248.
[30] Silverio, D. L.; Fu, P.; Carswell, E. L.; Snapper, M. L.; Hoveyda, A. H. Tetrahedron Lett. 2015, 56, 3489.
[31] Rainoldi, G.; Sacchetti, A.; Silvani, A.; Lesma, G. Org. Biomol. Chem. 2016, 14, 7768.
[32] Zhou, L.; Lin, L.; Ji, J.; Xie, M.; Liu, X.; Feng, X. Org. Lett. 2011, 13, 3056.
[33] Guo, Y.-L.; Bai, J.-F.; Peng, L.; Wang, L.-L.; Jia, L.-N.; Luo, X.-Y.; Tian, F.; Xu, X.-Y.; Wang, L.-X. J. Org. Chem. 2012, 77, 8338.
[34] Guo, Y.; Zhang, Y.; Qi, L.; Tian, F.; Wang, L. RSC Adv. 2014, 4, 27286.
[35] Yin, L.; Takada, H.; Kumagai, N.; Shibasaki, M. Angew. Chem., Int. Ed. 2013, 52, 7310.
[36] Nakamura, S.; Yamaji, R.; Hayashi, M. Chem.-Eur. J. 2015, 21, 9615.
[37] Trost, B. M.; Gnanamani, E.; Tracy, J. S.; Kalnmals, C. A. J. Am. Chem. Soc. 2017, 139, 18198.
[38] Wang, Z.-H.; You, Y.; Chen, Y.-Z.; Xu, X.-Y.; Yuan, W.-C. Org. Biomol. Chem. 2018, 16, 1636.
[39] Hitotsuyanagi, Y.; Takeda, E.; Fukaya, H.; Takeya, K. Tet-rahedron Lett. 2008, 49, 7376.
[40] Wang, A.-E.; Huang, P.-Q. Pure Appl. Chem. 2014, 86, 1227.
[41] Tuo, S.-C.; Ye, J.-L.; Wang, A.-E.; Huang, S.-Y.; Huang, P.-Q. Org. Lett. 2011, 13, 5270.
[42] Liu, X.-K.; Ye, J.-L.; Ruan, Y.-P.; Li, Y.-X.; Huang, P.-Q. J. Org. Chem. 2013, 78, 35.
[43] (a) Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567.
(b) Rassu, G.; Carta, P.; Pinna, L.; Battistini, L.; Zanardi, F.; Acquotti, D.; Casiraghi, G. Eur. J. Org. Chem. 1999, 1395.
[44] Miyatake-Ondozabal, H.; Bannwart, L. M.; Gademann, K. Chem. Commun. 2013, 49, 1921.
[45] Wehlauch, R.; Grendelmeier, S. M.; Miyatake-Ondozabal, H.; Sandtorv, A. H.; Scherer, M.; Gademann, K. Org. Lett. 2017, 19, 548.
[46] Ye, J.-L.; Zhang, Y.-F.; Liu, Y.; Zhang, J.-Y.; Ruan, Y.-P.; Huang, P.-Q. Org. Chem. Front. 2015, 2, 697.
[47] Oudeyer, S.; Dudot, B.; Royer, J. Heterocycles 2005, 65, 823.
[48] Ye, J.-L.; Chen, H.; Zhang, Y.-F.; Huang, P.-Q. Org. Chem. Front. 2016, 3, 683.
[49] Ye, J.-L.; Liu, Y.; Yang, Z.-P.; Huang, P.-Q. Chem. Commun. 2016, 52, 561.
[50] Ye, J.-L.; Liu, Y.; Zhang, Y.-F.; Yang, Z.-P.; Huang, P.-Q. Synthesis 2016, 48, 1684.
[51] Yoritate, M.; Takahashi, Y.; Tajima, H.; Ogihara, C.; Yokoyama, T.; Soda, Y.; Oishi, T.; Sato, T.; Chida, N. J. Am. Chem. Soc. 2017, 139, 18386.
[52] Zhou, T.; Gao, J.; Liu, G.; Guan, X.; An, D.; Zhang, S.; Zhang, G. Synlett 2018, 29, 2006.

基于杂环的不对称插烯Mannich反应及其在生物碱合成中的应用进展

Progress in Heterocycles-Based Asymmetric Vinylogous Mannich Reactions and Applications to the Synthesis of Alkaloids

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