Citation: Xi Wang, Fujie Liu, Tao Xu. Catalytic diastereoselective construction of multiple contiguous quaternary carbon stereocenters via [2 + 2] cycloaddition and mechanistic insight[J]. Chinese Chemical Letters, ;2023, 34(3): 107624. doi: 10.1016/j.cclet.2022.06.047 shu

Catalytic diastereoselective construction of multiple contiguous quaternary carbon stereocenters via [2 + 2] cycloaddition and mechanistic insight

Xi Wang ^a ,
Fujie Liu ^a ,
Tao Xu ^{a, b, *,}

a.
Molecular Synthesis Center & Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
b.
Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, China

xutao@ouc.edu.cn

Received Date: 12 April 2022
Revised Date: 15 June 2022
Accepted Date: 19 June 2022
Available Online: 23 June 2022

Figures(6)

Multiple contiguous quaternary carbon stereocenters (CQS) are highly challenging, yet important structural motifs in organic synthesis. Here, we describe a visible light induced catalytic [2 + 2] cycloaddition approach that constructed up to four CQS in a pentacyclic fused ring system diastereoselectively, from the readily accessible dienamides with pendent heteroaryls. Variously substituted dienamides have been cyclized with heteroaryls to provide a range of novel CQS-containing scaffolds (26 examples, up to 96% yield and > 20:1 dr ratio). Mechanistic studies revealed that it may proceed through an uncommon β-C radical initiated 7-endo cyclization from the biradical intermediate.
- Contiguous quaternary carbon stereocenters,
- [2 + 2] Cycloaddition,
- Fused ring system
1. [1]
  M. Buschleb, S. Dorich, S. Hanessian, et al., Angew. Chem. Int. Ed. 55 (2016) 4156–4186. doi: 10.1002/anie.201507549
2. [2]
  E.A. Peterson, L.E. Overman, Proc. Natl. Acad. Sci. U. S. A. 101 (2004) 11943–11948. doi: 10.1073/pnas.0402416101
3. [3]
  J. Christoffers, A. Baro, Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis, Wiley-VCH, 2005, pp. 1–46.
4. [4]
  A. Eggert, C. Etling, D. Lubken, et al., Molecules 25 (2020) 3841. doi: 10.3390/molecules25173841
5. [5]
  D.B. Clarke, S.F.R. Hinkley, R.T. Weavers, Tetrahedron Lett. 38 (1997) 4297. doi: 10.1016/S0040-4039(97)00884-8
6. [6]
  Y. Qu, Z. Wang, Z. Zhang, et al., J. Am. Chem. Soc. 142 (2020) 6511–6515. doi: 10.1021/jacs.0c02143
7. [7]
  C. Peng, P. Arya, Z. Zhou, et al., Angew. Chem. Int. Ed. 59 (2020) 13521–13525. doi: 10.1002/anie.202004177
8. [8]
  L. Rosenbaum, M. Hafner, T. Gaich, Angew. Chem. Int. Ed. 60 (2021) 2939–2942. doi: 10.1002/anie.202011298
9. [9]
  C.H. Huo, X.H. Su, Y.F. Wang, et al., Tetrahedron Lett. 48 (2007) 2721–2724. doi: 10.1016/j.tetlet.2007.02.063
10. [10]
  F.D. Araujo, L.C. Favaro, W.L. Araujo, et al., Eur. J. Org. Chem. 2012 (2012) 5225–5230.
11. [11]
  S.A. Kolesnikova, E.G. Lyakhova, A.I. Kalinovsky, et al., J. Nat. Prod. 82 (2019) 3196–3200. doi: 10.1021/acs.jnatprod.9b00824
12. [12]
  Z. Zhang, S. Chen, F. Tang, et al., J. Am. Chem. Soc. 143 (2021) 18287–18293. doi: 10.1021/jacs.1c08880
13. [13]
  A. Steven, L.E. Overman, Angew. Chem. Int. Ed. 46 (2007) 5488–5508. doi: 10.1002/anie.200700612
14. [14]
  R. Long, J. Huang, J. Gong, et al., Nat. Prod. Rep. 32 (2015) 1584. doi: 10.1039/C5NP00046G
15. [15]
  H. Zheng, Y. Wang, C. Xu, et al., Nat. Commun. 9 (2018) 1968. doi: 10.1038/s41467-018-04123-w
16. [16]
  F. Zhou, L. Zhu, B. Pan, et al., Chem. Sci. 11 (2020) 9341. doi: 10.1039/D0SC03249B
17. [17]
  D. Pierrot, I. Marek, Angew. Chem. Int. Ed. 59 (2020) 36–49. doi: 10.1002/anie.201903188
18. [18]
  Z. Xin, H. Wang, H. He, et al., Tetrahedron Lett. 71 (2021) 153029. doi: 10.1016/j.tetlet.2021.153029
19. [19]
  P. Ellerbrock, N. Armanino, M.K. Ilg, et al., Nat. Chem. 7 (2015) 879–882. doi: 10.1038/nchem.2336
20. [20]
  A.G. Kravina, E.M. Carreira, Angew. Chem. Int. Ed. 57 (2018) 13159. doi: 10.1002/anie.201807709
21. [21]
  F. Schneider, K. Samarin, S. Zinella, et al., Science 367 (2020) 676–681. doi: 10.1126/science.aay9173
22. [22]
  H. Wang, Q. Dong, Q. Xie, P. Tang, Chin. Chem. Lett. 31 (2020) 685–688. doi: 10.1016/j.cclet.2019.08.033
23. [23]
  J.J. Suo, J. Du, Y.J. Jiang, et al., Chin. Chem. Lett. 30 (2019) 1512–1514. doi: 10.1016/j.cclet.2019.04.028
24. [24]
  Z. Yang, Acc. Chem. Res. 54 (2021) 556–568. doi: 10.1021/acs.accounts.0c00709
25. [25]
  J. Xuan, W.J. Xiao, Angew. Chem. Int. Ed. 51 (2012) 6828. doi: 10.1002/anie.201200223
26. [26]
  M.H. Shaw, J. Twilton, D.W.C. MacMillan, J. Org. Chem. 81 (2016) 6898. doi: 10.1021/acs.joc.6b01449
27. [27]
  M.D. Karkas, J.A. Porco, C.R.J. Stephenson, Chem. Rev. 116 (2016) 9683. doi: 10.1021/acs.chemrev.5b00760
28. [28]
  K. Strieth-Kalthoff, M.J. James, M. Teders, et al., Chem. Soc. Rev. 47 (2018) 7190. doi: 10.1039/C8CS00054A
29. [29]
  M.K. Bogdos, E. Pinard, J.A. Murphy, Beilstein J. Org. Chem. 14 (2018) 2035. doi: 10.3762/bjoc.14.179
30. [30]
  R.C. McAtee, E.J. McClain, C.R.J. Stephenson, Trends Chem. 1 (2019) 111. doi: 10.1016/j.trechm.2019.01.008
31. [31]
  K.L. Skubi, T.R. Blum, T.P. Yoon, Chem. Rev. 116 (2016) 10035. doi: 10.1021/acs.chemrev.6b00018
32. [32]
  N.A. Romero, D.A. Nicewicz, Chem. Rev. 116 (2016) 10075. doi: 10.1021/acs.chemrev.6b00057
33. [33]
  S. Morris, T. Nguyen, N. Zheng, Visible Light Photocatalysis in Organic Chemistry, Wiley, 2018, pp. 129–158.
34. [34]
  M.J. Genzink, J.B. Kidd, W.B. Swords, et al., Chem. Rev. 122 (2021) 1654.
35. [35]
  S. Stegbauer, C. Jandl, T. Bach, Angew. Chem. Int. Ed. 57 (2018) 14593. doi: 10.1002/anie.201808919
36. [36]
  J. Mateos, A. Vega-Penaloza, P. Franceschi, et al., Chem. Sci. 11 (2020) 6532. doi: 10.1039/D0SC01569E
37. [37]
  M. Zhu, H. Xu, X. Zhang, et al., Angew. Chem. Int. Ed. 60 (2021) 7036. doi: 10.1002/anie.202016899
38. [38]
  C.G. Watson, A. Balanta, T.G. Elford, et al., J. Am. Chem. Soc. 136 (2014) 17370. doi: 10.1021/ja509029h
39. [39]
  R. Alam, C. Diner, S. Jonker, et al., Angew. Chem. Int. Ed. 55 (2016) 14417. doi: 10.1002/anie.201608605
40. [40]
  H. Ikezawa, C. Kutal, K. Yasufuku, et al., J. Am. Chem. Soc. 108 (1986) 1589. doi: 10.1021/ja00267a032
41. [41]
  Z. Lu, T.P. Yoon, Angew. Chem. Int. Ed. 51 (2012) 10329. doi: 10.1002/anie.201204835
42. [42]
  Y.Q. Zou, S.W. Duan, X.G. Meng, et al., Tetrahedron 68 (2012) 6914. doi: 10.1016/j.tet.2012.06.011
43. [43]
  M.E. Daub, H. Jung, B.J. Lee, et al., J. Am. Chem. Soc. 141 (2019) 9543. doi: 10.1021/jacs.9b04643
44. [44]
  A.E. Hurtley, Z. Lu, T.P. Yoon, Angew. Chem. Int. Ed. 53 (2014) 8991. doi: 10.1002/anie.201405359
45. [45]
  J. Zheng, W.B. Swords, H. Jung, et al., J. Am. Chem. Soc. 141 (2019) 13625. doi: 10.1021/jacs.9b06244
46. [46]
  D.A. Fort, T.J. Woltering, A.M. Alker, et al., J. Org. Chem. 79 (2014) 7152. doi: 10.1021/jo501302f
47. [47]
  H. Yu, S. Dong, Q. Yao, et al., Chem. Eur. J. 24 (2018) 19361. doi: 10.1002/chem.201804600
48. [48]
  M. Zhu, C. Zheng, X. Zhang, et al., ACS Catal. 10 (2020) 12618. doi: 10.1021/acscatal.0c03808
49. [49]
  Z. Zhang, D. Yi, M. Zhang, et al., ACS Catal. 10 (2020) 10149. doi: 10.1021/acscatal.0c01841
50. [50]
  M. Zhu, C. Zheng, X. Zhang, et al., J. Am. Chem. Soc. 141 (2019) 2636. doi: 10.1021/jacs.8b12965
51. [51]
  N. Arai, T. Ohkuma, J. Org. Chem. 85 (2020) 15717–15725. doi: 10.1021/acs.joc.0c02231
52. [52]
  M. Zhu, X.L. Huang, H. Xu, et al., CCS Chem. 3 (2021) 652–664. doi: 10.31635/ccschem.020.202000254
53. [53]
  N. Arai, T. Ohkuma, Org. Lett. 21 (2019) 1506. doi: 10.1021/acs.orglett.9b00309
54. [54]
  S. Poplata, A. Troster, Y.Q. Zou, et al., Chem. Rev. 116 (2016) 9748. doi: 10.1021/acs.chemrev.5b00723
55. [55]
  R. Remy, C.G. Bochet, Chem. Rev. 116 (2016) 9816. doi: 10.1021/acs.chemrev.6b00005
56. [56]
  Y.Z. Cheng, X. Zhang, S.L. You, Sci. Bull. 63 (2018) 809. doi: 10.1016/j.scib.2018.06.006
57. [57]
  Q.Q. Zhou, Y.Q. Zou, L.Q. Lu, et al., Angew. Chem. Int. Ed. 58 (2019) 1586. doi: 10.1002/anie.201803102
58. [58]
  M. Okumura, D. Sarlah, Eur. J. Org. Chem. (2020) 1259–1273.
59. [59]
  A.B. Flynn, W.W. Ogilvie, Chem. Rev. 107 (2007) 4698–4745. doi: 10.1021/cr050051k
60. [60]
  F. Strieth-Kalthoff, C. Henkel, M. Teders, et al., Chem 5 (2019) 2183. doi: 10.1016/j.chempr.2019.06.004
61. [61]
  J. Ma, S. Chen, P. Bellotti, et al., Science 371 (2021) 1338. doi: 10.1126/science.abg0720
62. [62]
  J. Zhang, X. Wang, T. Xu, Nat. Commun. 12 (2021) 3022. doi: 10.1038/s41467-021-23344-0
63. [63]
  Y. Wang, B. Qiu, L. Hu, et al., ACS Catal. 11 (2021) 9136. doi: 10.1021/acscatal.1c02480
64. [64]
  B. Qiu, X.T. Li, J.Y. Zhang, et al., Org. Lett. 20 (2018) 7689. doi: 10.1021/acs.orglett.8b03412
65. [65]
  N. Hu, H. Jung, Y. Zheng, et al., Angew. Chem. Int. Ed. 57 (2018) 6242–6246. doi: 10.1002/anie.201802891
66. [66]
  M.J. James, J.L. Schwarz, F. Strieth-Kalthoff, et al., J. Am. Chem. Soc. 140 (2018) 8624. doi: 10.1021/jacs.8b03302
67. [67]
  J. Zhao, J.L. Brosmer, Q. Tang, et al., J. Am. Chem. Soc. 139 (2017) 9807. doi: 10.1021/jacs.7b05277
68. [68]
  Y. Sun, L. Cui, Q. Li, et al., Chin. Chem. Lett. 33 (2022) 516–518. doi: 10.1016/j.cclet.2021.06.050
69. [69]
  D. Xiao, X. Zhao, J. Lei, M. Zhu, L. Xu, Chin. Chem. Lett. 32 (2021) 3031–3033. doi: 10.1016/j.cclet.2021.03.068
70. [70]
  R. Guo, H. Zhai, Y. Li, Chin. Chem. Lett. 32 (2021) 1400–1402. doi: 10.1016/j.cclet.2020.09.023
71. [71]
  H. Liu, Y. Wu, Q. Guo, et al., Chin. Chem. Lett., 32 (2021) 33–36. doi: 10.1016/j.cclet.2020.09.062
72. [72]
  H. Wang, S. Gu, Q. Yan, L. Ding, F.E. Chen, Green Synth. Catal. 1 (2020) 12–25. doi: 10.1016/j.gresc.2020.05.005
1. [1]
  Ruowen Liang , Chao Zhang , Guiyang Yan . Enhancing CO2 cycloaddition through ligand functionalization: A case study of UiO-66 metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(2): 100211-100211. doi: 10.1016/j.cjsc.2023.100211
2. [2]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
3. [3]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
4. [4]
  Xin Li , Wanting Fu , Ruiqing Guan , Yue Yuan , Qinmei Zhong , Gang Yao , Sheng-Tao Yang , Liandong Jing , Song Bai . Nucleophiles promotes the decomposition of electrophilic functional groups of tetracycline in ZVI/H₂O₂ system: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(10): 109625-. doi: 10.1016/j.cclet.2024.109625
5. [5]
  Ting-Ting Huang , Jin-Fa Chen , Juan Liu , Tai-Bao Wei , Hong Yao , Bingbing Shi , Qi Lin . A novel fused bi-macrocyclic host for sensitive detection of Cr₂O₇²⁻ based on enrichment effect. Chinese Chemical Letters, 2024, 35(7): 109281-. doi: 10.1016/j.cclet.2023.109281
6. [6]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
7. [7]
  Yifen He , Chao Qu , Na Ren , Dawei Liang . Enhanced degradation of refractory organics in ORR-EO system with a blue TiO₂ nanotube array modified Ti-based Ni-Sb co-doped SnO₂ anode. Chinese Chemical Letters, 2024, 35(8): 109262-. doi: 10.1016/j.cclet.2023.109262
8. [8]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
9. [9]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
10. [10]
  Xiuzheng Deng , Changhai Liu , Xiaotong Yan , Jingshan Fan , Qian Liang , Zhongyu Li . Carbon dots anchored NiAl-LDH@In₂O₃ hierarchical nanotubes for promoting selective CO₂ photoreduction into CH₄. Chinese Chemical Letters, 2024, 35(6): 108942-. doi: 10.1016/j.cclet.2023.108942
11. [11]
  Zhenyu Hu , Zhenchun Yang , Shiqi Zeng , Kun Wang , Lina Li , Chun Hu , Yubao Zhao . Cationic surface polarization centers on ionic carbon nitride for efficient solar-driven H₂O₂ production and pollutant abatement. Chinese Chemical Letters, 2024, 35(10): 109526-. doi: 10.1016/j.cclet.2024.109526
12. [12]
  Ziruo Zhou , Wenyu Guo , Tingyu Yang , Dandan Zheng , Yuanxing Fang , Xiahui Lin , Yidong Hou , Guigang Zhang , Sibo Wang . Defect and nanostructure engineering of polymeric carbon nitride for visible-light-driven CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(3): 100245-100245. doi: 10.1016/j.cjsc.2024.100245
13. [13]
  Yue Zhang , Xiaoya Fan , Xun He , Tingyu Yan , Yongchao Yao , Dongdong Zheng , Jingxiang Zhao , Qinghai Cai , Qian Liu , Luming Li , Wei Chu , Shengjun Sun , Xuping Sun . Ambient electrosynthesis of urea from carbon dioxide and nitrate over Mo₂C nanosheet. Chinese Chemical Letters, 2024, 35(8): 109806-. doi: 10.1016/j.cclet.2024.109806
14. [14]
  Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
15. [15]
  Xiaodan Wang , Yingnan Liu , Zhibin Liu , Zhongjian Li , Tao Zhang , Yi Cheng , Lecheng Lei , Bin Yang , Yang Hou . Highly efficient electrosynthesis of H₂O₂ in acidic electrolyte on metal-free heteroatoms co-doped carbon nanosheets and simultaneously promoting Fenton process. Chinese Chemical Letters, 2024, 35(7): 108926-. doi: 10.1016/j.cclet.2023.108926
16. [16]
  Meijuan Chen , Liyun Zhao , Xianjin Shi , Wei Wang , Yu Huang , Lijuan Fu , Lijun Ma . Synthesis of carbon quantum dots decorating Bi₂MoO₆ microspherical heterostructure and its efficient photocatalytic degradation of antibiotic norfloxacin. Chinese Chemical Letters, 2024, 35(8): 109336-. doi: 10.1016/j.cclet.2023.109336
17. [17]
  Binyang Qin , Mengqi Wang , Shimei Wu , Yining Li , Chilin Liu , Yufei Zhang , Haosen Fan . Carbon dots confined nanosheets assembled NiCo₂S₄@CDs cross-stacked architecture for enhanced sodium ion storage. Chinese Chemical Letters, 2024, 35(7): 108921-. doi: 10.1016/j.cclet.2023.108921
18. [18]
  Yuhao Ma , Yufei Zhou , Mingchuan Yu , Cheng Fang , Shaoxia Yang , Junfeng Niu . Covalently bonded ternary photocatalyst comprising MoSe₂/black phosphorus nanosheet/graphitic carbon nitride for efficient moxifloxacin degradation. Chinese Chemical Letters, 2024, 35(9): 109453-. doi: 10.1016/j.cclet.2023.109453
19. [19]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
20. [20]
  Jinjie Lu , Qikai Liu , Yuting Zhang , Yi Zhou , Yanbo Zhou . Antibacterial performance of cationic quaternary phosphonium-modified chitosan polymer in water. Chinese Chemical Letters, 2024, 35(9): 109406-. doi: 10.1016/j.cclet.2023.109406

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(243)
HTML views(26)

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