Citation: Ye Jianliang, Huang Peiqiang. Progress in Heterocycles-Based Asymmetric Vinylogous Mannich Reactions and Applications to the Synthesis of Alkaloids[J]. Chinese Journal of Organic Chemistry, ;2018, 38(9): 2215-2230. doi: 10.6023/cjoc201806005 shu

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

Corresponding author: Huang Peiqiang, pqhuang@xmu.edu.cn
Received Date: 3 June 2018
Revised Date: 22 August 2018
Available Online: 22 September 2018
Fund Project: the Natural Science Foundation of Fujian Province of China 2017J01021the National Natural Science Foundation of China 21332007Project 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)the Chinese Universities Scientific Fund 20720170092the National Natural Science Foundation of China 21472153the Chinese Universities Scientific Fund 20720180024the National Key R & D Program of China 2017YFA0207302

Figures(35)

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.
- vinylogous Mannich reaction,
- silyloxy pyrrole,
- silyloxy furan,
- imine,
- chiral auxiliary,
- asymmetric catalysis,
- alkaloid,
- asymmetric total synthesis
1. [1]
  Liu, Y.; Wu, Q.; Yin, D.; Li, D. Chin. J. Org. Chem. 2016, 36, 927(in Chinese).
2. [2]
  (a) Wehlauch, R.; Gademann, K. Asian J. Org. Chem. 2017, 6, 1146.
  (b) Martin, S. F. Adv. Heterocycl. Chem. 2013, 110, 73.
3. [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. [4]
  Sartori, A.; Dell'Amico, L.; Curti, C.; Battistini, L.; Pelosi, G.; Rassu, G.; Casiraghi, G.; Zanardi, F. Adv. Synth. Catal. 2011, 353, 3278. doi: 10.1002/adsc.201100572
5. [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. doi: 10.1039/c3ob42069h
6. [6]
  Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600. doi: 10.1021/cr900382t
7. [7]
  Ruan, S.-T.; Luo, J.-M.; Du, Y.; Huang, P.-Q. Org. Lett. 2011, 13, 4938. doi: 10.1021/ol2020384
8. [8]
  Bur, S. K.; Martin, S. F. Org. Lett. 2000, 2, 3445. doi: 10.1021/ol006464j
9. [9]
  Harding, K. E.; Southard, J. M. Tetrahedron:Asymmetry 2005, 16, 1845. doi: 10.1016/j.tetasy.2005.03.034
10. [10]
  Guo, L.-D.; Liang, P.; Zheng, J.-F.; Huang, P.-Q. Eur. J. Org. Chem. 2013, 2230.
11. [11]
  Liu, R.-C.; Wei, J.-H.; Wei, B.-G.; Lin, G.-Q. Tetrahedron:Asymmetry 2008, 19, 2731. doi: 10.1016/j.tetasy.2008.12.014
12. [12]
  Altenbach, H.-J.; Himmeldirk, K. Tetrahedron:Asymmetry 1995, 6, 1077. doi: 10.1016/0957-4166(95)00129-D
13. [13]
  Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachi, I.; Takahata, H. Tetrahedron:Asymmetry 2001, 12, 817. doi: 10.1016/S0957-4166(01)00136-7
14. [14]
  Nadin, A.; Sánchez López, J. M.; Neduvelil, J. G.; Thomas, S. R. Tetrahedron 2001, 57, 1861. doi: 10.1016/S0040-4020(00)01167-4
15. [15]
  Rao, V. U. B.; Jadhav, A. P.; Garad, D.; Singh, R. P. Org. Lett. 2014, 16, 648. doi: 10.1021/ol4037117
16. [16]
  Shi, Y.-H.; Wang, Z.; Shi, Y.; Deng, W.-P. Tetrahedron 2012, 68, 3649. doi: 10.1016/j.tet.2012.02.046
17. [17]
  Liu, L.-J.; Chen, L.-J.; Li, P.; Li, X.-B.; Liu, J.-T. J. Org. Chem. 2011, 76, 4675. doi: 10.1021/jo200119x
18. [18]
  Liu, L.-J.; Liu, J.-T. Tetrahedron 2014, 70, 1236. doi: 10.1016/j.tet.2013.12.071
19. [19]
  Yu, J.; Miao, Z.; Chen, R. Org. Biomol. Chem. 2011, 9, 1756. doi: 10.1039/c0ob01048k
20. [20]
  Tamura, O.; Takeda, K.; Mita, N.; Sakamoto, M.; Okamoto, I.; Morita, N.; Ishibashi, H. Org. Biomol. Chem. 2011, 9, 7411. doi: 10.1039/c1ob06067h
21. [21]
  Degiorgis, F.; Lombardo, M.; Trombini, C. Tetrahedron 1997, 53, 11721. doi: 10.1016/S0040-4020(97)00738-2
22. [22]
  Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772. doi: 10.1021/jo00299a017
23. [23]
  Yuan, Z.-L.; Jiang, J.-J.; Shi, M. Tetrahedron 2009, 65, 6001. doi: 10.1016/j.tet.2009.05.080
24. [24]
  Zhao, Q.-Y.; Yuan, Z.-L.; Shi, M. Tetrahedron:Asymmetry 2010, 21, 943. doi: 10.1016/j.tetasy.2010.05.025
25. [25]
  Zhao, Q.-Y.; Yuan, Z.-L.; Shi, M. Adv. Synth. Catal. 2011, 353, 637. doi: 10.1002/adsc.201000843
26. [26]
  Zheng, L.-S.; Li, L.; Yang, K.-F.; Zheng, Z.-J.; Xiao, X.-Q.; Xu, L.-W. Tetrahedron 2013, 69, 8777. doi: 10.1016/j.tet.2013.07.105
27. [27]
  Hayashi, M.; Sano, M.; Funahashi, Y.; Nakamura, S. Angew. Chem., Int. Ed. 2013, 52, 5557. doi: 10.1002/anie.201301917
28. [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. [29]
  Curti, C.; Battistini, L.; Ranieri, B.; Pelosi, G.; Rassu, G.; Casiraghi, G.; Zanardi, F. J. Org. Chem. 2011, 76, 2248. doi: 10.1021/jo1021234
30. [30]
  Silverio, D. L.; Fu, P.; Carswell, E. L.; Snapper, M. L.; Hoveyda, A. H. Tetrahedron Lett. 2015, 56, 3489. doi: 10.1016/j.tetlet.2015.04.006
31. [31]
  Rainoldi, G.; Sacchetti, A.; Silvani, A.; Lesma, G. Org. Biomol. Chem. 2016, 14, 7768. doi: 10.1039/C6OB01359G
32. [32]
  Zhou, L.; Lin, L.; Ji, J.; Xie, M.; Liu, X.; Feng, X. Org. Lett. 2011, 13, 3056. doi: 10.1021/ol200939t
33. [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. doi: 10.1021/jo301115t
34. [34]
  Guo, Y.; Zhang, Y.; Qi, L.; Tian, F.; Wang, L. RSC Adv. 2014, 4, 27286. doi: 10.1039/c4ra04824e
35. [35]
  Yin, L.; Takada, H.; Kumagai, N.; Shibasaki, M. Angew. Chem., Int. Ed. 2013, 52, 7310. doi: 10.1002/anie.201303119
36. [36]
  Nakamura, S.; Yamaji, R.; Hayashi, M. Chem.-Eur. J. 2015, 21, 9615. doi: 10.1002/chem.201500599
37. [37]
  Trost, B. M.; Gnanamani, E.; Tracy, J. S.; Kalnmals, C. A. J. Am. Chem. Soc. 2017, 139, 18198. doi: 10.1021/jacs.7b11361
38. [38]
  Wang, Z.-H.; You, Y.; Chen, Y.-Z.; Xu, X.-Y.; Yuan, W.-C. Org. Biomol. Chem. 2018, 16, 1636. doi: 10.1039/C7OB03117C
39. [39]
  Hitotsuyanagi, Y.; Takeda, E.; Fukaya, H.; Takeya, K. Tet-rahedron Lett. 2008, 49, 7376. doi: 10.1016/j.tetlet.2008.10.042
40. [40]
  Wang, A.-E.; Huang, P.-Q. Pure Appl. Chem. 2014, 86, 1227. doi: 10.1515/pac-2013-1210
41. [41]
  Tuo, S.-C.; Ye, J.-L.; Wang, A.-E.; Huang, S.-Y.; Huang, P.-Q. Org. Lett. 2011, 13, 5270. doi: 10.1021/ol202140y
42. [42]
  Liu, X.-K.; Ye, J.-L.; Ruan, Y.-P.; Li, Y.-X.; Huang, P.-Q. J. Org. Chem. 2013, 78, 35. doi: 10.1021/jo3014484
43. [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. [44]
  Miyatake-Ondozabal, H.; Bannwart, L. M.; Gademann, K. Chem. Commun. 2013, 49, 1921. doi: 10.1039/c3cc38783f
45. [45]
  Wehlauch, R.; Grendelmeier, S. M.; Miyatake-Ondozabal, H.; Sandtorv, A. H.; Scherer, M.; Gademann, K. Org. Lett. 2017, 19, 548. doi: 10.1021/acs.orglett.6b03716
46. [46]
  Ye, J.-L.; Zhang, Y.-F.; Liu, Y.; Zhang, J.-Y.; Ruan, Y.-P.; Huang, P.-Q. Org. Chem. Front. 2015, 2, 697. doi: 10.1039/C5QO00098J
47. [47]
  Oudeyer, S.; Dudot, B.; Royer, J. Heterocycles 2005, 65, 823. doi: 10.3987/COM-05-10335
48. [48]
  Ye, J.-L.; Chen, H.; Zhang, Y.-F.; Huang, P.-Q. Org. Chem. Front. 2016, 3, 683. doi: 10.1039/C6QO00022C
49. [49]
  Ye, J.-L.; Liu, Y.; Yang, Z.-P.; Huang, P.-Q. Chem. Commun. 2016, 52, 561. doi: 10.1039/C5CC07480K
50. [50]
  Ye, J.-L.; Liu, Y.; Zhang, Y.-F.; Yang, Z.-P.; Huang, P.-Q. Synthesis 2016, 48, 1684. doi: 10.1055/s-00000084
51. [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. doi: 10.1021/jacs.7b10944
52. [52]
  Zhou, T.; Gao, J.; Liu, G.; Guan, X.; An, D.; Zhang, S.; Zhang, G. Synlett 2018, 29, 2006. doi: 10.1055/s-0037-1610232
1. [1]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
2. [2]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
3. [3]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
4. [4]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
5. [5]
  Dengke Ma . Application of Integrating Fundamental Knowledge and Cutting-Edge Developments in the Teaching of Organic Synthesis: Taking the Asymmetric Meinwald Rearrangement as an Example. University Chemistry, 2026, 41(4): 67-74. doi: 10.12461/PKU.DXHX202502112
6. [6]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
7. [7]
  Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . Performance and Electrochemical Asymmetry Optimization of Hydrogen Electrode Supported Reversible Solid Oxide Cell. Acta Physico-Chimica Sinica, 2025, 41(1): 100005-0. doi: 10.3866/PKU.WHXB202309037
8. [8]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
9. [9]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
10. [10]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
11. [11]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
12. [12]
  Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
13. [13]
  Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
14. [14]
  Guilan He , Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122
15. [15]
  Jiatong Hu , Qiyi Wang , Ruiwen Tang , Jiajing Feng . Photocatalytic Journey of Perylene Diimides in a Competitive Arena. University Chemistry, 2025, 40(5): 328-333. doi: 10.12461/PKU.DXHX202407015
16. [16]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
17. [17]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . Thickness-Insensitive, Cyano-Modified Perylene Diimide Derivative as a Cathode Interlayer Material for High-Efficiency Organic Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 100027-0. doi: 10.3866/PKU.WHXB202406007
18. [18]
  Jingshuo Zhang , Yue Zhai , Ziyun Zhao , Jiaxing He , Wei Wei , Jing Xiao , Shichao Wu , Quan-Hong Yang . Research Progress of Functional Binders in Silicon-Based Anodes for Lithium-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(6): 2306006-0. doi: 10.3866/PKU.WHXB202306006
19. [19]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
20. [20]
  Linbao Zhang , Weisi Guo , Shuwen Wang , Ran Song , Ming Li . Electrochemical Oxidation of Sulfides to Sulfoxides. University Chemistry, 2024, 39(11): 204-209. doi: 10.3866/PKU.DXHX202401009

Get Citation

PDF

XML

Metrics

PDF Downloads(23)
Abstract views(2662)
HTML views(315)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142