Citation: Ying-Ying Sun, Bin Zhang, Liangbin Yu, Ranran Cui, Qingyang Zhao, Qing-Wei Zhang. Rhodium catalyzed asymmetric synthesis of Chiraphos derivatives[J]. Chinese Chemical Letters, ;2022, 33(12): 5084-5087. doi: 10.1016/j.cclet.2022.04.054 shu

Rhodium catalyzed asymmetric synthesis of Chiraphos derivatives

Ying-Ying Sun ^a ,
Bin Zhang ^a ,
Liangbin Yu ^b ,
Ranran Cui ^a ,
Qingyang Zhao ^{b, *,} ,
Qing-Wei Zhang ^{a, *,}

a.
Department of Chemistry, University of Science and Technology of China, Heifei 230026, China
b.
School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University, Shenzhen 518107, China

zhaoqy26@mail.sysu.edu.cn

qingweiz@ustc.edu.cn

Received Date: 4 February 2022
Revised Date: 20 April 2022
Accepted Date: 20 April 2022
Available Online: 26 April 2022

Figures(4)

Herein, we report a highly efficient versatile synthetic route to Chiraphos derivatives through Rh/Ph-bod catalyzed asymmetric addition of aryl boronic acids to phosphinyl dienes. Various substituted phosphinyl dienes, both on the parent skeleton and the phosphine atoms, were well tolerated with this method and provided chiral phosphine oxides in satisfied yield and up to 95% ee. The corresponding Chiraphos derivative displayed an advantage over Chiraphos in the representative Pd-catalyzed asymmetric 1,4-addition reaction.
- Rhodium,
- Phosphine,
- Diene ligand,
- 1,4-Addition,
- Chiraphos
1. [1]
  T.P. Dang, H.B. Kagan, Chem. Commun. (1971) 481.
2. [2]
  H.B. Kagan, T.P. Dang, J. Am. Chem. Soc. 94 (1972) 6429–6433. doi: 10.1021/ja00773a028
3. [3]
  H.B. Kagan, N. Langlois, T.P. Dang, J. Organomet. Chem. 90 (1975) 353–365. doi: 10.1016/S0022-328X(00)88129-2
4. [4]
  B.D. Vineyard, W.S. Knowles, M.J. Sabacky, G.L. Bachman, D.J. Weinkauff, J. Am. Chem. Soc. 99 (1977) 5946–5952. doi: 10.1021/ja00460a018
5. [5]
  R. Noyori, T. Ohkuma, M. Kitamura, et al., J. Am. Chem. Soc. 109 (1987) 5856–5858. doi: 10.1021/ja00253a051
6. [6]
  W. Tang, X. Zhang, Chem. Rev. 103 (2003) 3029–3070. doi: 10.1021/cr020049i
7. [7]
  W. Zhang, X. Zhang, Bisphosphacycles–from DuPhos and BPE to a diverse set of broadly applied ligands, in: Q.L. Zhou (Ed. ), Privileged Chiral Ligands and Catalysts, Wiley-VCH, Weinheim, 2011, pp. 55–91.
8. [8]
  M. Dutartre, J. Bayardon, S. Jugé, Chem. Soc. Rev. 45 (2016) 5771–5794. doi: 10.1039/C6CS00031B
9. [9]
  T. Imamoto, Chem. Rec. 16 (2016) 2659–2673. doi: 10.1002/tcr.201600098
10. [10]
  H. Guo, Y.C. Fan, Z. Sun, Y. Wu, O. Kwon, Chem. Rev. 118 (2018) 10049–10293. doi: 10.1021/acs.chemrev.8b00081
11. [11]
  H. Ni, W.L. Chan, Y. Lu, Chem. Rev. 118 (2018) 9344–9411. doi: 10.1021/acs.chemrev.8b00261
12. [12]
  G. Xu, C.H. Senanayake, W. Tang, Acc. Chem. Res. 52 (2019) 1101–1112. doi: 10.1021/acs.accounts.9b00029
13. [13]
  X.H. Kang, C. Qian, H. Yang, et al., Green Synth. Catal. 3 (2022) 185–189. doi: 10.1016/j.gresc.2022.01.002
14. [14]
  R. Mutin, W. Abboud, J.M. Bass, D. Sinou, J. Mol. Catal. 33 (1985) 47–59. doi: 10.1016/0304-5102(85)85016-1
15. [15]
  I. Ojima, N. Clos, C. Bastos, Tetrahedron 45 (1989) 6901–6939. doi: 10.1016/S0040-4020(01)89159-6
16. [16]
  R. Kadyrov, T.H. Riermeier, U. Dingerdissen, V. Tararov, A. Börner, J. Org. Chem. 68 (2003) 4067–4070. doi: 10.1021/jo020690k
17. [17]
  C.J. Scheuermann née Taylor, C. Jaekel, Adv. Synth. Catal. 350 (2008) 2708–2714. doi: 10.1002/adsc.200800462
18. [18]
  P. Mauleon, J.C. Carretero, Org. Lett. 6 (2004) 3195–3198. doi: 10.1021/ol048690p
19. [19]
  T. Nishikata, Y. Yamamoto, N. Miyaura, Chem. Commun. (2004) 1822–1823.
20. [20]
  T. Nishikata, Y. Yamamoto, N. Miyaura, Chem. Lett. 34 (2005) 720–721. doi: 10.1246/cl.2005.720
21. [21]
  T. Nishikata, Y. Yamamoto, N. Miyaura, Chem. Lett. 36 (2007) 1442–1443. doi: 10.1246/cl.2007.1442
22. [22]
  K. Kurihara, N. Sugishita, K. Oshita, et al., J. Organomet. Chem. 692 (2007) 428–435. doi: 10.1016/j.jorganchem.2006.04.042
23. [23]
  X.Q. Yu, T. Shirai, Y. Yamamoto, N. Miyaura, Chem. Asian J. 6 (2011) 932–937. doi: 10.1002/asia.201000589
24. [24]
  M. Yamaguchi, T. Shima, T. Yamagishi, M. Hida, Tetrahedron: Asymmetry 2 (1991) 663–666.
25. [25]
  E. Gomez-Bengoa, N.M. Heron, M.T. Didiuk, C.A. Luchaco, A.H. Hoveyda, J. Am. Chem. Soc. 120 (1998) 7649–7650. doi: 10.1021/ja980499l
26. [26]
  C. Jaekel, R Paciello, US Patent 7534921, 2006.
27. [27]
  K. Campbell, C.A. Johnson, R. McDonald, et al., Angew. Chem. Int. Ed. 43 (2004) 5967–5971. doi: 10.1002/anie.200461139
28. [28]
  M. Sugiuchi, Y. Shichibu, K. Konishi, Angew. Chem. Int. Ed. 57 (2018) 7855–7859. doi: 10.1002/anie.201804087
29. [29]
  M.D. Fryzuk, B. Bosnich, J. Am. Chem. Soc. 99 (1977) 6262–6267. doi: 10.1021/ja00461a014
30. [30]
  J. Jansen, B.L. Feringa, Tetrahedron: Asymmetry 1 (1990) 719–720. doi: 10.1016/S0957-4166(00)82382-4
31. [31]
  M. Jin, M. Nakamura, Chem. Lett. 42 (2013) 1035–1037. doi: 10.1246/cl.130375
32. [32]
  U. Matteoli, V. Beghetto, C. Schiavon, A. Scrivanti, G. Menchi, Tetrahedron: Asymmetry 8 (1997) 1403–1409. doi: 10.1016/S0957-4166(97)00132-8
33. [33]
  V. Beghetto, U. Matteoli, A. Scrivanti, Chem. Commun. (2000) 155–156.
34. [34]
  V. Hornillos, C. Vila, E. Otten, B.L. Feringa, Angew. Chem. Int. Ed. 54 (2015) 7867–7871. doi: 10.1002/anie.201502987
35. [35]
  W.J. Yue, J.Z. Xiao, S. Zhang, L. Yin, Angew. Chem. Int. Ed. 59 (2020) 7057–7062. doi: 10.1002/anie.201916076
36. [36]
  A. Kondoh, Ishikawa S, M. Terada, Org. Biomol. Chem. 18 (2020) 7814–7817. doi: 10.1039/D0OB01778G
37. [37]
  M. Sakai, H. Hayashi, N. Miyaura, Organometallics 16 (1997) 4229–4231. doi: 10.1021/om9705113
38. [38]
  Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, N. Miyaura, J. Am. Chem. Soc. 120 (1998) 5579–5580. doi: 10.1021/ja980666h
39. [39]
  T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara, J. Am. Chem. Soc. 124 (2002) 5052–5058. doi: 10.1021/ja012711i
40. [40]
  T. Hayashi, K. Yamasaki, Chem. Rev. 103 (2003) 2829–2844. doi: 10.1021/cr020022z
41. [41]
  A. Kina, H. Iwamura, T. Hayashi, J. Am. Chem. Soc. 128 (2006) 3904–3905. doi: 10.1021/ja060225v
42. [42]
  N. Lefevre, J.L. Brayer, B. Folléas, S. Darses, Org. Lett. 15 (2013) 4274–4276. doi: 10.1021/ol402059w
43. [43]
  T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc. 125 (2003) 11508–11509. doi: 10.1021/ja037367z
44. [44]
  R. Shintani, K. Ueyama, I. Yamada, T. Hayashi, Org. Lett. 6 (2004) 3425–3427. doi: 10.1021/ol048421z
45. [45]
  N. Tokunaga, Y. Otomaru, K. Okamoto, et al., J. Am. Chem. Soc. 126 (2004) 13584–13585. doi: 10.1021/ja044790e
46. [46]
  Y. Otomaru, K. Okamoto, R. Shintani, T. Hayashi, J. Org. Chem. 70 (2005) 2503–2508. doi: 10.1021/jo047831y
47. [47]
  R. Shintani, T. Kimura, T. Hayashi, Chem. Commun. (2005) 3213–3214.
48. [48]
  R. Shintani, K. Okamoto, T. Hayashi, Org. Lett. 7 (2005) 4757–4759. doi: 10.1021/ol051978+
49. [49]
  R. Shintani, A. Tsurusaki, K. Okamoto, T. Hayashi, Angew. Chem. Int. Ed. 44 (2005) 3909–3912. doi: 10.1002/anie.200500843
50. [50]
  R. Shintani, Y. Ichikawa, T. Hayashi, et al., Org. Lett. 9 (2007) 4643–4645. doi: 10.1021/ol702125q
51. [51]
  S. Sörgel, N. Tokunaga, K. Sasaki, K. Okamoto, T. Hayashi, Org. Lett. 10 (2008) 589–592. doi: 10.1021/ol702879u
52. [52]
  R. Shintani, T. Hayashi, Aldrichim. Acta 42 (2009) 31–38.
53. [53]
  C.G. Feng, M.H. Xu, G.Q. Lin, Synlett (2011) 1345–1356.
54. [54]
  S. Abele, R. Inauen, D. Spielvogel, C. Moessner, J. Org. Chem. 77 (2012) 4765–4773. doi: 10.1021/jo3005638
55. [55]
  M. Nagamoto, T. Nishimura, ACS Catal. 7 (2017) 833–847. doi: 10.1021/acscatal.6b02495
56. [56]
  J.P. Chen, M.H. Xu, Org. Biomol. Chem. 18 (2020) 4569–4574. doi: 10.1039/D0OB00616E
57. [57]
  J. -P. Chen, Y. Li, C. Liu, et al., Org. Lett. 23 (2021) 571–577. doi: 10.1021/acs.orglett.0c04099
58. [58]
  R. Crabtree, Acc. Chem. Res. 12 (1979) 331–337. doi: 10.1021/ar50141a005
59. [59]
  R.H. Crabtree, M.W. Davis, J. Org. Chem. 51 (1986) 2655–2661. doi: 10.1021/jo00364a007
60. [60]
  J.M. Brown, Angew. Chem. Int. Ed. 26 (1987) 190–203. doi: 10.1002/anie.198701901
61. [61]
  D. Herault, N. Duc Hanh, D. Nuel, G. Buono, Chem. Soc. Rev. 44 (2015) 2508–2528. doi: 10.1039/C4CS00311J
62. [62]
  H. Brisset, Y. Gourdel, P. Pellon, M. Lecorre, Tetrahedron Lett. 34 (1993) 4523–4526. doi: 10.1016/0040-4039(93)88075-T
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