Citation: Wang Zhihui, Zhang Zhenfeng, Liu Yangang, Zhang Wanbin. Development of the Asymmetric Hydrogenation of Enol Esters[J]. Chinese Journal of Organic Chemistry, ;2016, 36(3): 447-459. doi: 10.6023/cjoc201512009 shu

Development of the Asymmetric Hydrogenation of Enol Esters

Wang Zhihui ^a ,
Zhang Zhenfeng ^a,*,, ,
Liu Yangang ^a ,
Zhang Wanbin ^a,b,*,,

a.
School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240
b.
School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Corresponding author: Zhang Zhenfeng, Zhang Wanbin, wanbin@sjtu.edu.cn
Received Date: 7 December 2015
Revised Date: 6 January 2016

Fund Project: the Science and Technology Commission of Shanghai Municipality 14XD1402300the National Natural Science Foundation of China 21572131

Figures(10)

Chiral alcohols are an important class of compounds and possess a broad array of applications, thus their asymmetric preparation is an important area of research in the field of organic synthesis. Amongst methodologies for the preparation of such compounds, catalytic asymmetric hydrogenation has gained widespread interest due to its efficiency, environmentally friendliness and economic advantages, and is gradually becoming a technology with great potential for the industrial preparation of chiral alcohols. This review provides the first overview for the catalytic asymmetric hydrogenation of enol esters for the synthesis of chiral alcohols. A comprehensive and up-to-date introduction are given for a number of different substrates. A thorough analysis is provided concerning the advantages and disadvantages of different chiral ligands and their transition-metal complexes. Finally, a brief discussion relating to developments and potential areas of further research concerning new substrates, new ligands and new catalytic metals, is presented.
- enol esters,
- chiral alcohols,
- asymmetric hydrogenation,
- Ru-catalyzed,
- Rh-catalyzed
1. [1]
  de Vries, J. G.; Elsevier, C. J. Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim, Germany, 2007.
  (b) Ma, Y.; Zhang, Y. J.; Zhang, W. Chin. J. Org. Chem. 2007, 27, 289 (in Chinese). (马元辉, 张勇健, 张万斌, 有机化学, 2007, 27, 289.)
  (c) Blaser, H.-U.; Federsel, H.-J. Asymmetric Catalysis on Industrial Scale, 2nd ed., Wiley-VCH, Weinheim, Germany, 2010.
  (d) Xie, J.-H.; Zhou, Q.-L. Acta Chim. Sinica 2012, 70, 1427 (in Chinese). (谢建华, 周其林, 化学学报, 2012, 70, 1427.)
  (e) Etayo, P.; Vidal-Ferran, A. Chem. Soc. Rev. 2013, 42, 728.(f) Wang, Y.; Zhang, Z.; Zhang, W. Chin. J. Org. Chem. 2015, 35, 528 (in Chinese).
  (王英杰, 张振锋, 张万斌, 有机化学, 2015, 35, 528.)
2. [2]
  Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
  (b) Klingler, F. D. Acc. Chem. Res. 2007, 40, 1367.
3. [3]
  Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1978, 100, 5491. doi: 10.1021/ja00485a037
4. [4]
  Koenig, K. E.; Bachman, G. L.; Vineyard, B. D. J. Org. Chem. 1980, 45, 2362. doi: 10.1021/jo01300a019
5. [5]
  Brown, J. M.; Murrer, B. A. J. Chem. Soc., Perkin Trans. 2 1982, 489.
6. [6]
  Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518. doi: 10.1021/ja00022a047
7. [7]
  Lotz, M.; Ireland, T.; Perea, J. J. A.; Knochel, P. Tetrahedron: Asymmetry 1999, 10, 1839. doi: 10.1016/S0957-4166(99)00182-2
8. [8]
  Ireland, T.; Tappe, K.; Grossheimann, G.; Knochel, P. Chem. Eur. J. 2002, 8, 843.
  (b) Lotz, M.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 4708.
9. [9]
  Gavrilov, K. N.; Benetsky, E. B.; Boyko, V. E.; Rastorguev, E. A.; Davankov, V. A.; Schäffner, B.; Börner, A. Chirality 2010, 22, 844. doi: 10.1002/chir.20845
10. [10]
  Schmidt, U.; Langner, J.; Kirschbaum, B.; Braun, C. Synthesis 1994, 1138.
11. [11]
  Lüttenberg, S.; Ta, T. D.; von der Heyden, J.; Scherkenberk, J. Eur. J. Org. Chem. 2013, 1824.
12. [12]
  Stephan, M.; Šterk, D.; Mohar, B. Adv. Synth. Catal. 2009, 351, 2779.
  (b) Zupančič, B.; Mohar, B.; Stephan, M. Org. Lett. 2010, 12, 1296.
  (c) Zupančič, B.; Mohar, B.; Stephan, M. Org. Lett. 2010, 12, 3022.
13. [13]
  Burk, M. J.; Kalberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345. doi: 10.1021/ja974278b
14. [14]
  Han, X.; Jiang, X.-J.; Civiello, R. L.; Degnan, A. P.; Chaturvedula, P. V.; Macor, J. E.; Dubowchik, G. M. J. Org. Chem. 2009, 74, 3993. doi: 10.1021/jo900368k
15. [15]
  Liu, Y.; Sandoval, C. A.; Yamaguchi, Y.; Zhang, X.; Wang, Z.; Kato, K.; Ding, K. J. Am. Chem. Soc. 2006, 128, 14212. doi: 10.1021/ja063350f
16. [16]
  Dong, C.; Wang, Y.; Zhu, Y. Z. Bioorg. Med. Chem. 2009, 17, 3499.
  (b) Pan, L.-L.; Wang, J.; Jia, Y.-L.; Zheng, H.-M.; Wang, Y.; Zhu, Y.-Z. Int. J. Mol. Sci. 2015, 16, 628.
17. [17]
  Wang, Q.; Huang, W.; Yuan, H.; Cai, Q.; Chen, L.; Lv, H.; Zhang, X. J. Am. Chem. Soc. 2014, 136, 16120. doi: 10.1021/ja509005e
18. [18]
  Boaz, N. W. Tetrahedron Lett. 1998, 39, 5505. doi: 10.1016/S0040-4039(98)00730-8
19. [19]
  Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489. doi: 10.1021/jo000066c
20. [20]
  Tang, W.; Liu, D.; Zhang, X. Org. Lett. 2003, 5, 205. doi: 10.1021/ol0272592
21. [21]
  Liu, D.; Zhang, X. Eur. J. Org. Chem. 2005, 646.
22. [22]
  Zhang, X.; Huang, K.; Hou, G.; Cao, B.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 6421. doi: 10.1002/anie.201002990
23. [23]
  Pullmann, T.; Engendahl, B.; Zhang, Z.; Hölscher, M.; Zanotti-Gerosa, A.; Dyke, A.; Franciò, G.; Leitner, W. Chem. Eur. J. 2010, 16, 7517. doi: 10.1002/chem.201000063
24. [24]
  Knorad, T. M.; Schmitz, P.; Leitner, W.; Franciò, G. Chem. Eur. J. 2013, 19, 13299. doi: 10.1002/chem.201303066
25. [25]
  Robert, T.; Abiri, Z.; Sandee, A. J.; Schmalz, H.-G.; Reek, J. N. H. Tetrahedron: Asymmetry 2010, 21, 2671. doi: 10.1016/j.tetasy.2010.10.026
26. [26]
  Etayo, P.; Núñez-Rico, J. L.; Fernández-Pérez, H.; Vidal-Ferran, A. Chem. Eur. J. 2011, 17, 13978.
  (b) Etayo, P.; Núñez-Rico, J. L.; Vidal-Ferran, A. Organometallics 2011, 30, 6718.
  (c) Núñez-Rico, J. L.; Etayo, P.; Fernández-Pérez, H.; Vidal-Ferran, A. Adv. Synth. Catal. 2012, 354, 3025.
27. [27]
  Fernández-Pérez, H.; Benet-Buchholz, J.; Vidal-Ferran, A. Org. Lett. 2013, 15, 3634.
  (b) Fernández-Pérez, H.; Benet-Buchholz, J.; Vidal-Ferran, A. Chem. Eur. J. 2014, 20, 15375.
  (c). Lao, J. R. Benet-Buchholz, J.; Vidal-Ferran, A. Organometallics 2014, 33, 2960.
28. [28]
  Kleman, P.; González-Liste, P. J.; García-Garrido, S. E.; Cadierno, V.; Pizzano, A. Chem. Eur. J. 2013, 19, 16209.
  (b) Kleman, P.; González-Liste, P. J.; García-Garrido, S. E.; Cadierno, V.; Pizzano, A. ACS. Catal. 2014, 4, 4398.
29. [29]
  Reetz, M. T.; Goossen, L. J.; Meiswinkel, A.; Paetzold, J.; Jensen, J. F. Org. Lett. 2003, 5, 3099. doi: 10.1021/ol035076p
30. [30]
  Mamone, P.; Grünberg, M. F.; Fromm, A.; Khan, B. A.; Gooβen, L. J. Org. Lett. 2012, 14, 3716. doi: 10.1021/ol301563g
31. [31]
  Alegre, S.; Alberico, E.; Pàmies, O.; Diéguez, M. Tetrahedron: Asymmetry 2014, 25, 258. doi: 10.1016/j.tetasy.2013.12.010
32. [32]
  Jiang, X.-B.; van den Berg, M.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. Tetrahedron: Asymmetry 2004, 15, 2223. doi: 10.1016/j.tetasy.2004.05.002
33. [33]
  Panella, L.; Feringa, B. L.; de Vries, J. G.; Minnaard, A. J. Org. Lett. 2005, 7, 4177. doi: 10.1021/ol051559c
34. [34]
  Enthaler, S.; Erre, G.; Junge, K.; Michalik, D.; Spannenberg, A.; Marras, F.; Gladiali, S.; Beller, M. Tetrahedron: Asymmetry 2007, 18, 1288. doi: 10.1016/j.tetasy.2007.06.001
35. [35]
  Liu, Y.; Wang, Z.; Ding, K. Tetrahedron 2012, 68, 7581. doi: 10.1016/j.tet.2012.05.096
36. [36]
  Schmitz, C.; Leiter, W.; Franciò, G. Eur. J. Org. Chem. 2015, 2889.
37. [37]
  Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takaya, H. J. Org. Chem. 1995, 60, 357. doi: 10.1021/jo00107a014
38. [38]
  Kuroki, Y.; Asada, D.; Sakamaki, Y.; Iseki, K. Tetrahedron Lett. 2000, 41, 4603. doi: 10.1016/S0040-4039(00)00643-2
39. [39]
  Wu, S.; Wang, W.; Tang, W.; Lin, M.; Zhang, X. Org. Lett. 2002, 4, 4495. doi: 10.1021/ol027010k
40. [40]
  Qiu, L.; Wu, J.; Chan, S.; Au-Yeung, T. T.-L.; Ji, J.-X.; Guo, R.; Pai, C.-C.; Zhou, Z.; Li, X.; Fan, Q.-H.; Chan, A. S. C. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5815. doi: 10.1073/pnas.0307774101
41. [41]
  Le Gendre, P.; Braun, T.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1996, 61, 8453. doi: 10.1021/jo961413e
42. [42]
  Fehr, M. J.; Consiglio, G.; Scalone, M.; Schmid, R. J. Org. Chem. 1999, 64, 5768. doi: 10.1021/jo982215l
43. [43]
  Broger, E. A.; Burkart, W.; Hennig, M.; Scalone, M.; Schmid, R. Tetrahedron: Asymmetry 1998, 9, 4043. doi: 10.1016/S0957-4166(98)00423-6
44. [44]
  Jiang, Q; Xiao, D; Zhang, Z; Cao, P; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 516. doi: 10.1002/(ISSN)1521-3773
45. [45]
  Pignataro, L.; Bovio, C.; Civera, M.; Piarulli, U.; Gennari, C. Chem. Eur. J. 2012, 18, 10368. doi: 10.1002/chem.201201032
46. [46]
  Burk, M. J.; Stammers, T. A.; Straub, J. A. Org. Lett. 1999, 1, 387. doi: 10.1021/ol9906099
47. [47]
  Liu, H.; Zhou, Y.-G.; Yu, Z.-K.; Xiao, W.-J.; Liu, S.-H.; He, H.-W. Tetrahedron 2006, 60, 11207.
48. [48]
  Gridnev, I. D.; Higashi, N.; Imamoto, T. J. Am. Chem. Soc. 2001, 123, 4631.
  (b). Gridnev, I. D.; Higashi, N.; Imamoto, T. Organometallics 2001, 20, 4542.
  (c) Gridnev, I. D.; Yasutake, M.; Imamoto, T.; Beletskaya, I. P. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5385.
  (d) Imamoto, T.; Yashio, K.; Crépy, K. V. L.; Katagiri, K.; Takahashi, H.; Kouchi, M.; Gridnev, I. D. Organometallics 2006, 25, 908.
  (e). Gridnev, I. D.; Imamoto, T.; Hoge, G.; Kouchi, M.; Takahashi, H. J. Am. Chem. Soc. 2008, 130, 2560.
  (f). Tamura, K.; Sugiya, M.; Yoshida, K.; Yanagisawa, A.; Imamoto, T. Org. Lett. 2010, 12, 4400.
49. [49]
  Rubio, M.; Suárez, A.; Álvarez, E.; Pizzano, A. Chem. Commun. 2005, 628.
  (b) Rubio, M.; Vargas, S.; Suárez, A.; Álvarez, E.; Pizzano, A. Chem. Eur. J. 2007, 13, 1821.
50. [50]
  Wassenaar, J.; Reek, J. N. H. J. Org. Chem. 2009, 74, 8403.
  (b) Wassenaar, J.; Kuil, M.; Lutz, M.; Spek, A. L.; Reek, J. N. H. Chem. Eur. J. 2010, 16, 6509.
51. [51]
  Wang, D.-Y.; Hu, X.-P.; Huang, J.-D.; Deng, J.; Yu, S.-B.; Duan, Z.-C.; Xu, X.-F.; Zheng, Z. Angew. Chem., Int. Ed. 2007, 46, 7810.
  (b) Qiu, M.; Hu, X.-P.; Huang, J.-D.; Wang, D.-Y.; Deng, J.; Yu, S.-B.; Duan, Z.-C.; Zheng, Z. Adv. Synth. Catal. 2008, 350, 2683.
  (c) Wang, D.-Y.; Huang, J.-D.; Hu, X.-P.; Deng, J.; Yu, S.-B.; Duan, Z.-C.; Zheng, Z. J. Org. Chem. 2008, 73, 2011.
52. [52]
  Fernández-Pérez, H.; Pericàs, M. A.; Vidal-Ferran, A. Adv. Synth. Catal. 2008, 350, 1984. doi: 10.1002/adsc.v350:13
53. [53]
  Vargas, S.; Suárez, A.; Álvarez, E.; Pizzano, A. Chem. Eur. J. 2008, 14, 9856.
  (b) Chávez, M. Á.; Vargas, S.; Suárez, A.; Álvarez, E.; Pizzano, A. Adv. Synth. Catal. 2011, 353, 2775.
54. [54]
  Konno, T.; Shimizu, K.; Ogata, K.; Fukuzawa, S.-I. J. Org. Chem. 2012, 77, 3318. doi: 10.1021/jo300129m
55. [55]
  Sun, T.; Zhang, X. Adv. Synth. Catal. 2012, 354, 3211. doi: 10.1002/adsc.201200224
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]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
8. [8]
  Hailang JIA , Pengcheng JI , Hongcheng LI . Preparation and performance of nickel doped ruthenium dioxide electrocatalyst for oxygen evolution. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1632-1640. doi: 10.11862/CJIC.20240398
9. [9]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
10. [10]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
11. [11]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
12. [12]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
13. [13]
  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
14. [14]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
15. [15]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
16. [16]
  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
17. [17]
  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
18. [18]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
19. [19]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
20. [20]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1414)
HTML views(222)

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