Citation: Li Shuailong, Li Zhuangxing, You Cai, Lv Hui, Zhang Xumu. Recent Advances in Asymmetric Hydroformylation[J]. Chinese Journal of Organic Chemistry, ;2019, 39(6): 1568-1582. doi: 10.6023/cjoc201903044 shu

Recent Advances in Asymmetric Hydroformylation

Li Shuailong ^a ,
Li Zhuangxing ^a ,
You Cai ^a ,
Lv Hui ^a,b,d,, ,
Zhang Xumu ^c

a.
Key Laboratory of Biomedical Polymers of Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
b.
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
c.
Department of Chemistry, Southern University of Science and Technology, Shenzhen Grubbs Institute, Shenzhen 518055
d.
Sauvage Center for Molecular Sciences, Wuhan University, Wuhan 430072

Corresponding author: Lv Hui, huilv@whu.edu.cn
Received Date: 22 March 2019
Revised Date: 23 April 2019
Available Online: 6 June 2019
Fund Project: the Natural Science Foundation of Hubei Province 2018CFB430Project supported by the National Natural Science Foundation of China (No. 21871212) and the Natural Science Foundation of Hubei Province (No. 2018CFB430)the National Natural Science Foundation of China 21871212

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Asymmetric hydroformylation is one of the most important reactions for preparation of chiral aldehydes from alkenes. Recently, significant progress has been made in this field and a series of new ligands have been developed. Asymmetric hydroformylation of several important alkenes has been achieved, offering efficient and concise methods for the synthesis of chiral aldehydes. In this review, the achievements of asymmetric hydroformylation of typical alkenes and the development of ligands for asymmetric hydroformylation are summarized.
- alkene,
- asymmetric hydroformylation,
- aldehyde,
- chiral phosphine ligand,
- rhodium
1. [1]
2. [2]
  Naqvi, S. Oxo Alcohols. Process Economics Program Report 21E, SRI Consulting, Menlo Park, CA, 2010.
3. [3]
  Botteghi, C.; Consiglio, G.; Pino, P. Chimia 1972, 26, 141.
4. [4]
  (a) Ogata, I.; Ikeda, Y. Chem. Lett. 1972, 487.
  (b) Tanaka, M.; Watanabe, Y.; Mitsudo, T.-A.; Yamamoto, K.; Takeeami, Y. Chem. Lett. 1972, 483.
5. [5]
  Salomon, C.; Consiglio, G.; Botteghi, C.; Pino, P. Chimia 1973, 27, 215.
6. [6]
  (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033.
  (b) Nozaki, K.; Nanno, T.; Takaya, H. J. Organomet. Chem. 1997, 527, 103.
  (c) Lambers-Verstappen, M. M. H.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 478.
  (d) Tanaka, R.; Nakano, K.; Nozaki, K. J. Org. Chem. 2007, 72, 8671.
7. [7]
  (a) Yan, Y.; Zhang, X. J. Am. Chem. Soc. 2006, 128, 7198.
  (b) Zhang, X.; Cao, B.; Yan, Y.; Yu, S.; Ji, B. M.; Zhang, X. Chem.-Eur. J. 2010, 16, 871.
  (c) Zhang, X.; Cao, B.; Yu, S.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 4047.
  (d) Wei, B.; Chen, C.; You, C.; Lv, H.; Zhang, X. Org. Chem. Front. 2017, 4, 288.
8. [8]
  (a) Noonan, G. M.; Fuentes, J. A.; Cobley, C. J.; Clarke, M. L. Angew. Chem., Int. Ed. 2012, 51, 2477.
  (b) Noonan, G. M.; Cobley, C. J.; Mahoney, T.; Clarke, M. L. Chem. Commun. 2014, 50, 1475.
9. [9]
  (a) Babin, J. E.; Whiteker, G. T. US 5360938, 1993 [Chem. Abstr. 1995, 122, 186609].
  (b) Buisman, G. J. H.; Vos, E. J.; Kamer, P. C. J.; Van Leeuwen, P. W. N. M. J. Chem. Soc., Dalton Trans. 1995, 409.
10. [10]
  (a) Cobley, C. J.; Klosin, J.; Qin, C.; Whiteker, G. T. Org. Lett. 2004, 6, 3277.
  (b) Cobley, C. J.; Gardner, K.; Klosin, J.; Praquin, C.; Hill, C.; Whiteker, G. T.; Zanotti-Gerosa, A. J. Org. Chem. 2004, 69, 4031.
11. [11]
  (a) Clark, T. P.; Landis, C. R.; Freed, S. L.; Klosin, J.; Abboud, K. A. J. Am. Chem. Soc. 2005, 127, 5040.
  (b) Watkins, A. L.; Landis, C. R. J. Am. Chem. Soc. 2010, 132, 10306.
  (c) Adint, T. T.; Landis, C. R. J. Am. Chem. Soc. 2014, 136, 7943.
12. [12]
  Axtell, A. T.; Cobley, C. J.; Klosin, J.; Whiteker, G. T.; ZanottiGerosa, A.; Abboud, K. A. Angew. Chem., Int. Ed. 2005, 44, 4. doi: 10.1002/anie.200462726
13. [13]
  Xu, K.; Zheng, X.; Wang, Z.; Zhang, X. Chem.-Eur. J. 2014, 20, 4357. doi: 10.1002/chem.201304684
14. [14]
  Hua, Z.; Vassar, V. C.; Choi, H.; Ojima, I. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5411. doi: 10.1073/pnas.0307101101
15. [15]
  (a) Kuil, M.; Goudriaan, P. E.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Commun. 2006, 4679.
  (b) Bellini, R.; Reek, J. N. H. Chem.-Eur. J. 2012, 18, 13510.
16. [16]
  Breit, B.; Breuninger, D. J. Am. Chem. Soc. 2004, 126, 10244. doi: 10.1021/ja0467364
17. [17]
  Worthy, A. D.; Joe, C. L.; Lightburn, T. E.; Tan, K. L. J. Am. Chem. Soc. 2010, 132, 14757. doi: 10.1021/ja107433h
18. [18]
  (a) Zhao, B.; Peng, X.; Wang, Z.; Xia, C.; Ding, K. Chem.-Eur. J. 2008, 14, 7847.
  (b) Peng, X.; Wang, Z.; Xia, C.; Ding, K. Tetrahedron Lett. 2008, 49, 4862.
19. [19]
  Jouffroy, M.; Gramage-Doria, R.; Armspach, D.; Sémeril, D.; Oberhauser, W.; Matt, D.; Toupet, L. Angew. Chem., Int. Ed. 2014, 53, 3937. doi: 10.1002/anie.201311291
20. [20]
  Thomas, P. J.; Axtell, A. T.; Klosin, J.; Peng, W.; Rand, C. L.; Clark, T. P.; Landis, C. R.; Abboud, K. A. Org. Lett. 2007, 9, 2665. doi: 10.1021/ol070900l
21. [21]
  Tan, R. C.; Zheng, X.; Qu, B.; Sarer, C. A.; Fandrick, K. R.; Senanayake, C. H.; Zhang, X. M. Org. Lett. 2016, 18, 3346. doi: 10.1021/acs.orglett.6b01452
22. [22]
  Schmitz, C.; Holthusen, K.; Leitner, W.; Franció, G. ACS Catal. 2016, 6, 1584. doi: 10.1021/acscatal.5b02846
23. [23]
  Breeden, S.; Cole-Hamilton, D. J.; Foster, D. F.; Schwarz, G. J.; Wills, M. Angew. Chem., Int. Ed. 2000, 39, 4106. doi: 10.1002/(ISSN)1521-3773
24. [24]
  Zhang, X.; Cao, B.; Yu, S.; Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 4047. doi: 10.1002/anie.201000955
25. [25]
  Yu, Z.; Eno, M. S.; Annis, A. H.; Morken, J. P. Org. Lett. 2015, 17, 3264. doi: 10.1021/acs.orglett.5b01421
26. [26]
  Dingwall, P.; Fuentes, J. A.; Crawford, L.; Slawin, A. M. Z.; Bühl, M.; Clarke, M. L. J. Am. Chem. Soc. 2017, 139, 15921. doi: 10.1021/jacs.7b09164
27. [27]
  Iu, L.; Fuentes, J. A.; Janka, M. E.; Fontenot, K. J.; Clarke, M. L. Angew. Chem., Int. Ed. 2019, 58, 2120. doi: 10.1002/anie.v58.7
28. [28]
  Horiuchi, T.; Ohta, T.; Shirakawa. E.; Nozaki, K.; Takaya, H. J. Org. Chem. 1997, 62, 4285. doi: 10.1021/jo9624051
29. [29]
  (a) Diéguez, M.; Pamies, O.; Claver, C. Chem. Commun. 2005, 1221.
  (b) Gual, A.; Godard, C.; Castillón, S.; Claver, C. Adv. Synth. Catal. 2010, 352, 463.
30. [30]
  (a) Chikkali, S. H.; Bellini, R.; Berthon-Gelloz, G.; van der Vlugt, J. I.; de Bruin, B.; Reek, J. N. H. Chem. Commun. 2010, 46, 1244.
  (b) Chikkali, S. H.; Bellini, R.; de Bruin, B.; van der Vlugt, J. I.; Reek, J. N. H. J. Am. Chem. Soc. 2012, 134, 6607.
31. [31]
  Rovira, L.; Vaquero, M.; Vidal-Ferran, A. J. Org. Chem. 2015, 80, 10397. doi: 10.1021/acs.joc.5b01805
32. [32]
  Watkins, A. L.; Hashiguchi, B. G.; Landis, C. R. Org. Lett. 2008, 10, 4553. doi: 10.1021/ol801723a
33. [33]
  Fuentes, J. A.; Pittaway, R.; Clarke, M. L. Chem.-Eur. J. 2015, 21, 10645. doi: 10.1002/chem.v21.30
34. [34]
  Sherill, W. M.; Rubin, M. J. Am. Chem. Soc. 2008, 130, 13804. doi: 10.1021/ja805059f
35. [35]
  You, C.; Wei, B.; Li, X.; Yang, Y.; Liu, Y.; Lv, H.; Zhang, X. Angew. Chem., Int. Ed. 2016, 55, 6511. doi: 10.1002/anie.201601478
36. [36]
  Sakai, N.; Nozaki, K.; Takaya, H. J. Chem. Soc., Chem. Commun. 1994, 395.
37. [37]
  (a) McDonald, R. I.; Wong, G. W.; Neupane, R. P.; Stahl, S. S.; Landis, C. R. J. Am. Chem. Soc. 2010, 132, 14027.
  (b) Abrams, M. L.; Foarta, F.; Landis, C. R. J. Am. Chem. Soc. 2014, 136, 14583.
38. [38]
  Clemens, A. J. L.; Burke, S. D. J. Org. Chem. 2012, 77, 2983. doi: 10.1021/jo300025t
39. [39]
  (a) Worthy, A. M.; Joe, C. L.; Lightburn, T. E.; Tan, K. L. J. Am. Chem. Soc. 2010, 132, 14757.
  (b) Joe, C. L.; Blaisdell, T. P.; Geoghan, A. F.; Tan, K. L. J. Am. Chem. Soc. 2014, 136, 8556.
40. [40]
  Gadzikwa, T.; Bellini, R.; Dekker, H. L.; Reek, J. N. H. J. Am. Chem. Soc. 2012, 134, 2860. doi: 10.1021/ja211455j
41. [41]
  You, C.; Li, X.; Yang, Y.; Yang, Y.-S.; Tan, X.; Li, S.; Wei, B.; Lv, H.; Chung, L.-W.; Zhang, X. Nat. Commun. 2018, 9, 2045. doi: 10.1038/s41467-018-04277-7
42. [42]
  Deng, Y.; Wang, H.; Sun, Y.; Wang, X. ACS Catal. 2015, 5, 6828. doi: 10.1021/acscatal.5b01300
43. [43]
  Kollár, L.; Bakos, J.; Tóth, I.; Heil, B. J. Organomet. Chem. 1988, 350, 277. doi: 10.1016/0022-328X(88)80383-8
44. [44]
  Consiglio, G.; Roncetti, L. Chirality 1991, 3, 341. doi: 10.1002/(ISSN)1520-636X
45. [45]
  Ojima, I.; Takai, M.; Takahashi, T. WO 078766, 2004 [Chem. Abstr. 2004, 141, 260889].
46. [46]
  You, C.; Li, S.; Li, X.; Lan, J.; Yang, Y.; Chung, L.-W.; Lv, H.; Zhang, X. J. Am. Chem. Soc. 2018, 140, 4977. doi: 10.1021/jacs.8b00275
47. [47]
  Wang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2011, 133, 19080. doi: 10.1021/ja2092689
48. [48]
  Zheng, X.; Cao, B.; Liu, T.; Zhang, X. Adv. Synth. Catal. 2013, 355, 679. doi: 10.1002/adsc.201200960
49. [49]
  Gladiali, S.; Pinna, L. Tetrahedron:Asymmetry 1990, 1, 693. doi: 10.1016/S0957-4166(00)82375-7
50. [50]
  Lee, C. W.; Alper, H. J. Org. Chem. 1995, 60, 499. doi: 10.1021/jo00108a007
51. [51]
  Wang, X.; Buchwald, S. L. J. Org. Chem. 2013, 78, 3429. doi: 10.1021/jo400115r
52. [52]
  Fanfoni, L.; Diab, L.; Smejkal, T.; Breit, B. Chimia 2014, 68, 371. doi: 10.2533/chimia.2014.371
53. [53]
  Eshon, J.; Foarta, F.; Landis, C. R.; Schomaker, J. M. J. Org. Chem. 2018, 83, 10207. doi: 10.1021/acs.joc.8b01431
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