Citation: Yang Yun, Liu Huihui, Liu Xiaobing, Liu Tiantian, Zhu Yuqin, Zhang Anan, Wang Tao, Hua Yuanzhao, Wang Mincan, Mao Guoliang, Liu Lantao. Asymmetric Synthesis of Axial Chiral Vinylarenes Fearturing Oxindole Moiety via Tandem Carbopalladation/C-H Olefination[J]. Chinese Journal of Organic Chemistry, ;2019, 39(6): 1655-1664. doi: 10.6023/cjoc201903050 shu

Asymmetric Synthesis of Axial Chiral Vinylarenes Fearturing Oxindole Moiety via Tandem Carbopalladation/C-H Olefination

Yang Yun ^a ,
Liu Huihui ^a ,
Liu Xiaobing ^a ,
Liu Tiantian ^b ,
Zhu Yuqin ^b ,
Zhang Anan ^b ,
Wang Tao ^b ,
Hua Yuanzhao ^c ,
Wang Mincan ^c ,
Mao Guoliang ^a,, ,
Liu Lantao ^b,c,,

a.
College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing 163318
b.
College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000
c.
College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Corresponding author: Mao Guoliang, maoguoliang@nepu.edu.cn Liu Lantao, liult05@iccas.ac.cn
Received Date: 24 March 2019
Revised Date: 10 May 2019
Available Online: 15 June 2019
Fund Project: the Program of Science and Technology Innovation Talents of Henan Province 2018JQ0011the National Natural Science Foundation of China 21572126Project supported by the National Natural Science Foundation of China (No. 21572126), the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 14HASTIT016) and the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011)the Program for Science & Technology Innovation Talents in Universities of Henan Province 14HASTIT016

Figures(5)

Due to the lower configuration stability of vinylarenes, arsing from the relatively lower rotational barriers, their catalytic asymmetric synthesis remains a daunting task. Oxindoles moiety are privileged framework of natural products and building blocks of bioactive molecules as well as pharmaceuticals. The asymmetric synthesis of axial chiral vinylarenes fearturing oxindole moiety via sequential carbopalladation/C-H olefination from readily available materials with palladium catalysis has been developed. (4R, 5R)-(-)-2, 2-Dimethyl-α, α, α', α'-tetraphenyl-1, 3-dioxolane-4, 5-dimethanol (TADDOL)-derived phosphoramidite gave products with good yield and moderate ee value. The erosion of optical purity was not observed even after heating the product for 10 h at 110℃, which indicates the excellent stability of the chiral axial.
- asymmetric synthesis,
- axial chirality,
- vinyl-arenes,
- carbopalladation,
- C-H olefination,
- oxindole
1. [1]
  (a) Bringmann, G.; Menche, D. Acc. Chem. Res. 2001, 34, 615.
  (b) Bringmann, G.; Gulder, T.; Gulder, T. A. M.; Breuning, M. Chem. Rev. 2011, 111, 563.
2. [2]
  (a) LaPlante, S. R.; Edwards, P. J.; Fader, L. D.; Jakalian, A.; Hucke, O. ChemMedChem 2011, 6, 505.
  (b) Clayden, J.; Moran, W. J.; Edwards, P. J.; S. LaPlante, R. Angew. Chem., Int. Ed. 2009, 48, 6398.
  (c) Glunz, P. W. Bioorg. Med. Chem. Lett. 2018, 28, 53.
3. [3]
  (a) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
  (b) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
  (c) Kočovský, P.; Vyskočil, Š.; Smrčina, M. Chem. Rev. 2003, 103, 3213.
  (d) Akiyama, T. Chem. Rev. 2007, 107, 5744.
4. [4]
  For selected reviews, see: (a) Bringmann, G.; Price Mortimer, A. J.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384.
  (b) Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193.
  (c) Quinonero, O.; Bressy, C.; Bugaut, X. Angew. Chem., Int. Ed. 2014, 53, 10861.
  (d) Zhang, D.; Wang, Q. Coord. Chem. Rev. 2015, 286, 1.
  (e) Wencel-Delord, J.; Panossian, A.; Leroux, F. R.; Colobert, F. Chem. Soc. Rev. 2015, 44, 3418.
  (f) Loxq, P.; Manoury, E.; Poli, R.; Deydier, E.; Labande, A. Coord. Chem. Rev. 2016, 308, 131.
  (g) Wang, Y.-B.; Tan, B. Acc. Chem. Res. 2018, 51, 534.
  (h) Zilate, B.; Castrogiovanni, A.; Sparr, C. ACS Catal. 2018, 8, 2981.
5. [5]
  Tanaka, K.; Shibata, T. In Transition-Metal-Mediated Aromatic Ring Construction, Ed.: Tanaka, K., John Wiley & Sons, Inc., Hoboken, New Jersey, 2013, pp. 255~279.
6. [6]
  (a) Baker, R. W.; Hambley, T. W.; Turner, P.; Wallace, B. J. Chem. Commun. 1996, 2571.
  (b)Hattori, T.; Date, M.; Sakurai, K.; Morohashi, N.; Kosugi, H.; Miyano, S. Tetrahedron Lett. 2001, 42, 8035.
7. [7]
  (a) Feng, J.; Li, B.; He, Y.; Gu, Z. Angew. Chem., Int. Ed. 2016, 55, 2186.
  (b) Feng, J.; Li, B.; Jiang, J.; Zhang, M.; Ouyang, W.; Li, C.; Fu, Y.; Gu, Z. Chin. J. Chem. 2018, 36, 11.
8. [8]
  Jolliffe, J. D.; Armstrong, R. J.; Smith, M. D. Nat. Chem. 2017, 9, 558. doi: 10.1038/nchem.2710
9. [9]
  Zheng, S.-C.; Wu, S.; Zhou, Q.; Chung, L. W.; Ye, L.; Tan, B. Nat. Commun. 2017, 8, 15238. doi: 10.1038/ncomms15238
10. [10]
  Jia, S. Q.; Chen, Z. L.; Zhang, N.; Tan, Y.; Liu, Y. D.; Deng, J.; Yan, H. L. J. Am. Chem. Soc. 2018, 140, 7056. doi: 10.1021/jacs.8b03211
11. [11]
12. [12]
  Pd-catalyzed: (a) Li, S.-X.; Ma, Y.-N.; Yang, S.-D. Org. Lett. 2017, 19, 842.
  (b) He, C.; Hou, M.; Zhu, Z.; Gu, Z. ACS Catal. 2017, 7, 5316.
  (c) Yao, Q.-J.; Zhang, S.; Zhan, B.-B.; Shi, B.-F. Angew. Chem., Int. Ed. 2017, 56, 6617.
  (d) Liao, G.; Yao, Q.-J.; Zhang, Z.-Z.; Wu, Y.-J.; Huang, D.-Y.; Shi, B.-F. Angew. Chem., Int. Ed. 2018, 57, 3665.
  (e) Zhang, S.; Yao, Q.-J.; Liao, G.; Li, X.; Li, H.; Chen, H.-M.; Hong, X.; Shi, B.-F. ACS Catal. 2019, 9, 1956.
  Rh-catalyzed:
  (f) Kakiuchi, F.; Gendre, P. Le; Yamada, A.; Ohtaki, H.; Murai, S. Tetrahedron: Asymmetry 2000, 11, 2647.
  (g) Zheng, J.; You, S.-L. Angew. Chem., Int. Ed. 2014, 53, 13244.
  (h) Zheng, J.; Cui, W.-J.; Zheng, C.; You, S.-L. J. Am. Chem. Soc. 2016, 138, 5242.
13. [13]
  Pd-catalyzed: (a) Yamaguchi, K.; Yamaguchi, J.; Studer, A.; Itami, K. Chem. Sci. 2012, 3, 2165.
  (b) Yamaguchi, K.; Kondo, H.; Yamaguchi, J.; Itami, K. Chem. Sci. 2013, 4, 3753.
  (c) Nishimoto, Y.; Kondo, H.; Yamaguchi, K.; Yokogawa, D.; Yamaguchi, J.; Itami, K.; Irle, S. J. Org. Chem. 2017, 82, 4900.
  (d) Newton, C. G.; Jennifer Kuziola, E. B.; Wodrich, M. D.; Cramer, N. Angew. Chem., Int. Ed. 2018, 57, 11040.
  Rh-catalyzed: (e) Jia, Z.-J.; Merten, C.; Gontla, R.; Daniliuc, C. G.; Antonchick, A. P.; Waldmann, H. Angew. Chem., Int. Ed. 2017, 56, 2429.
  (f) Shibuya, T.; Shibata, Y.; Noguchi, K.; Tanaka, K. Angew. Chem., Int. Ed. 2011, 50, 3963.
14. [14]
  (a) Sasaki, E.; Miyoshi, K.; Nozawa, Y.; Kanda, A.; Nakano, K.; Yamasaki, Y.; Miyake, H.; Matsuura, N. Pharmacology 2001, 63, 17.
  (b) Yu, L.-F.; Li, Y.-Y.; Su, M.-B.; Zhang, M.; Zhang, W.; Zhang, L.-N.; Pang, T.; Zhang, R.-T.; Liu, B.; Li, J.-Y.; Li, J.; Nan, F.-J. ACS Med. Chem. Lett. 2013, 4, 475.
  (c) Pal, A.; Ganguly, A.; Ghosh, A.; Yousuf, M.; Rathore, B.; Banerjee, R.; Adhikari, S. ChemMedChem 2014, 9, 727.
15. [15]
  (a) Liu, L.; Zhang, A.-A.; Zhao, R.-J.; Li, F.; Meng, T.-J.; Ishida, N.; Murakami, M.; Zhao, W.-X. Org. Lett. 2014, 16, 5336.
  (b) Liu, L.; Zhang, A.-A.; Wang, Y.; Zhang, F.; Zuo, Z.; Zhao, W.-X.; Feng, C.-L.; Ma, W. Org. Lett. 2015, 17, 2046.
16. [16]
  Pinto, A.; Neuville, L.; Retailleau, P.; Zhu, J. P. Org. Lett. 2006, 8, 4927. doi: 10.1021/ol062022h
17. [17]
  Zhou, Y.; Zhang, X.; Zhang, Y.; Ruan, L.; Zhang, J.; Zhangnegrerie, D.; Du, Y. Org. Lett. 2017, 19, 150. doi: 10.1021/acs.orglett.6b03455
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