Citation: Jiajun Lu, Zhehui Liao, Tongxiang Cao, Shifa Zhu. Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol[J]. Chinese Chemical Letters, ;2025, 36(1): 109842. doi: 10.1016/j.cclet.2024.109842 shu

Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol

Jiajun Lu ^a ,
Zhehui Liao ^a ,
Tongxiang Cao ^{a, *,} ,
Shifa Zhu ^{a, b, c, *,}

a.
Key Laboratory of Functional Molecular Engineering of Guang-dong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China
b.
School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, China
c.
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

caotx@scut.edu.cn

zhusf@scut.edu.cn

Received Date: 9 December 2023
Revised Date: 20 March 2024
Accepted Date: 29 March 2024
Available Online: 30 March 2024

Figures(5)

Axially chiral binaphthol have achieved great success in asymmetric catalysis. Compared to α-binaphthol, axially chiral aryl-β-naphthol are far less reported. Here, we report a method of asymmetric catalysis to construct β-naphthol with up to 99% yield, 95.5:4.5 enantiomeric ratio, using alkynyl esters as precursors and chiral phosphonic acid (CPA)/Lewis acid as catalysts. Key steps involve oxygen transfer and de novo arene formation to set up the chiral axis. Moreover, this methodology provides a versatile platform for structurally divergent synthesis of atroposelective β-naphthol analogs, which are widely found in bioactive molecules and asymmetric catalysts.
- Synergistic catalysis,
- Atropisomerism,
- Aryl-β-naphthol,
- Enantioselectivity,
- Tandem reaction
1. [1]
  J.K. Cheng, S.H. Xiang, S. Li, L. Ye, B. Tan, Chem. Rev. 121 (2021) 4805–4902. doi: 10.1021/acs.chemrev.0c01306
2. [2]
  D. Liang, W. Xiao, S. Lakhdar, J. Chen, Green Synth. Catal. 3 (2022) 212–218. doi: 10.1016/j.gresc.2022.06.003
3. [3]
  X.L. Min, X.L. Zhang, R. Shen, Q. Zhang, Y. He, Org. Chem. Front. 9 (2022) 2280–2292. doi: 10.1039/d1qo01699g
4. [4]
  Y. Chen, S. Yekta, A.K. Yudin, Chem. Rev. 103 (2003) 3155–3212. doi: 10.1021/cr020025b
5. [5]
  R.S. Griffith, F.B. Peck Jr., Antibiot. Annu. 3 (1955) 619–622.
6. [6]
  Y.F. Hallock, K.P. Manfredi, J.W. Blunt, et al., J. Org. Chem. 59 (1994) 6349–6355. doi: 10.1021/jo00100a042
7. [7]
  M. Nakajima, K. Kanayama, I. Miyoshi, S.I. Hashimoto, Tetrahedron Lett. 36 (1995) 9519–9520. doi: 10.1016/0040-4039(95)02063-2
8. [8]
  H. Egami, K. Matsumoto, T. Oguma, T. Kunisu, T. Katsuki, J. Am. Chem. Soc. 132 (2010) 13633–13635. doi: 10.1021/ja105442m
9. [9]
  S. Narute, R. Parnes, F.D. Toste, D. Pappo, J. Am. Chem. Soc. 138 (2016) 16553–16560. doi: 10.1021/jacs.6b11198
10. [10]
  H. Kang, C. Torruellas, J. Liu, M.C. Kozlowski, Org. Lett. 20 (2018) 5554–5558. doi: 10.1021/acs.orglett.8b02183
11. [11]
  J.M. Tian, A.F. Wang, J.S. Yang, et al., Angew. Chem. Int. Ed. 58 (2019) 11023–11027. doi: 10.1002/anie.201903435
12. [12]
  Y.H. Chen, D.J. Cheng, J. Zhang, et al., J. Am. Chem. Soc. 137 (2015) 15062–15065. doi: 10.1021/jacs.5b10152
13. [13]
  H. Gao, Q.L. Xu, C. Keene, et al., Angew. Chem. Int. Ed. 55 (2016) 566–571. doi: 10.1002/anie.201508419
14. [14]
  J.Z. Wang, J. Zhou, C. Xu, et al., J. Am. Chem. Soc. 138 (2016) 5202–5205. doi: 10.1021/jacs.6b01458
15. [15]
  Z.J. Jia, C. Merten, R. Gontla, et al., Angew. Chem. Int. Ed. 56 (2017) 2429–2434. doi: 10.1002/anie.201611981
16. [16]
  Y.S. Jang, Ł. Woźniak, J. Pedroni, N. Cramer, Angew. Chem. Int. Ed. 57 (2018) 12901–12905. doi: 10.1002/anie.201807749
17. [17]
  L.W. Qi, S. Li, S.H. Xiang, J. Wang, B. Tan, Nat. Catal. 2 (2019) 314–323. doi: 10.1038/s41929-019-0247-1
18. [18]
  G. Coombs, M.H. Sak, S.J. Miller, Angew. Chem. Int. Ed. 59 (2020) 2875–2880. doi: 10.1002/anie.201913563
19. [19]
  J.W. Zhang, L.W. Qi, S. Li, S.H. Xiang, B. Tan, Chin. J. Chem. 38 (2020) 1503–1514. doi: 10.1002/cjoc.202000358
20. [20]
  G. Bringmann, D. Menche, Acc. Chem. Res. 34 (2001) 615–624. doi: 10.1021/ar000106z
21. [21]
  K. Mori, T. Itakura, T. Akiyama, Angew. Chem. Int. Ed. 55 (2016) 11642–11646. doi: 10.1002/anie.201606063
22. [22]
  C. Yu, H. Huang, X. Li, Y. Zhang, W. Wang, J. Am. Chem. Soc. 138 (2016) 6956–6959. doi: 10.1021/jacs.6b03609
23. [23]
  G.A.I. Moustafa, Y. Oki, S. Akai, Angew. Chem. Int. Ed. 57 (2018) 10278–10282. doi: 10.1002/anie.201804161
24. [24]
  L.a. Hu, Y. Zhang, G.Q. Chen, et al., Org. Lett. 21 (2019) 5575–5580. doi: 10.1021/acs.orglett.9b01907
25. [25]
  B.A. Jones, T. Balan, J.D. Jolliffe, C.D. Campbell, M.D. Smith, Angew. Chem. Int. Ed. 58 (2019) 4596–4600. doi: 10.1002/anie.201814381
26. [26]
  G. Yang, D. Guo, D. Meng, J. Wang, Nat. Commun. 10 (2019) 3062. doi: 10.1038/s41467-019-10878-7
27. [27]
  M. Furusawa, K. Arita, T. Imahori, et al., Tetrahedron Lett. 54 (2013) 7107–7110. doi: 10.1016/j.tetlet.2013.10.080
28. [28]
  Y. Liu, X. Wu, S. Li, et al., Angew. Chem. Int. Ed. 57 (2018) 6491–6495. doi: 10.1002/anie.201801824
29. [29]
  S. Jia, S. Li, Y. Liu, W. Qin, H. Yan, Angew. Chem. Int. Ed. 58 (2019) 18496–18501. doi: 10.1002/anie.201909214
30. [30]
  R.M. Witzig, V.C. Fäseke, D. Häussinger, C. Sparr, Nat. Catal. 2 (2019) 925–930. doi: 10.1038/s41929-019-0345-0
31. [31]
  J. Zhang, M. Simon, C. Golz, M. Alcarazo, Angew. Chem. Int. Ed. 59 (2020) 5647–5650. doi: 10.1002/anie.201915456
32. [32]
  Y. Fukuyama, M. Toyota, Y. Asakawa, J. Chem. Soc., Chem. Commun. (1988) 1341–1342.
33. [33]
  G.N. Zhang, L.Y. Zhong, S.W. Annie Bligh, et al., Phytochemistry 66 (2005) 1113–1120. doi: 10.1016/j.phytochem.2005.04.001
34. [34]
  J. Chen, X. Gong, J. Li, et al., Science 360 (2018) 1438–1442. doi: 10.1126/science.aat4210
35. [35]
  W. Wen, L. Chen, M.J. Luo, et al., J. Am. Chem. Soc. 140 (2018) 9774–9780. doi: 10.1021/jacs.8b06676
36. [36]
  N.E. Schore, Chem. Rev. 88 (1988) 1081–1119. doi: 10.1021/cr00089a006
37. [37]
  F. Alonso, I.P. Beletskaya, M. Yus, Chem. Rev. 104 (2004) 3079–3160. doi: 10.1021/cr0201068
38. [38]
  J. Guo, Z. Cheng, J. Chen, X. Chen, Z. Lu, Acc. Chem. Res. 54 (2021) 2701–2716. doi: 10.1021/acs.accounts.1c00212
39. [39]
  L. Chen, K. Chen, S. Zhu, Chem 4 (2018) 1208–1262. doi: 10.1016/j.chempr.2018.02.001
40. [40]
  L. Chen, Z. Liu, S. Zhu, Org. Biomol. Chem. 16 (2018) 8884–8898. doi: 10.1039/c8ob02348d
41. [41]
  Z.X. Zhang, T.Y. Zhai, L.W. Ye, Chem. Catal. 1 (2021) 1378–1412. doi: 10.1016/j.checat.2021.09.011
42. [42]
  Y.D. Shao, M.M. Dong, Y.A. Wang, et al., Org. Lett. 21 (2019) 4831–4836. doi: 10.1021/acs.orglett.9b01731
43. [43]
  P. Nimnual, K. Norseeda, B. Akkachairin, et al., Asian J. Org. Chem. 7 (2018) 932–945. doi: 10.1002/ajoc.201800025
44. [44]
  B. Akkachairin, J. Tummatorn, N. Supantanapong, et al., J. Org. Chem. 82 (2017) 3727–3740. doi: 10.1021/acs.joc.7b00198
45. [45]
  H. Egami, J. Asada, K. Sato, et al., J. Am. Chem. Soc. 137 (2015) 10132–10135. doi: 10.1021/jacs.5b06546
46. [46]
  C. Min, D. Seidel, Chem. Soc. Rev. 46 (2017) 5889–5902. doi: 10.1039/C6CS00239K
47. [47]
  X. Xu, L. Peng, X. Chang, C. Guo, J. Am. Chem. Soc. 143 (2021) 21048–21055. doi: 10.1021/jacs.1c11044
48. [48]
  T. Zhou, P.F. Qian, J.Y. Li, et al., J. Am. Chem. Soc. 143 (2021) 6810–6816. doi: 10.1021/jacs.1c03111
49. [49]
  J.Y. Li, P.P. Xie, T. Zhou, et al., ACS Catal. 12 (2022) 9083–9091. doi: 10.1021/acscatal.2c00962
50. [50]
  V.S. Raut, M. Jean, N. Vanthuyne, et al., J. Am. Chem. Soc. 139 (2017) 2140–2143. doi: 10.1021/jacs.6b11079
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