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

  • 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.
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    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

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