Citation: Chen Wei, Guo Renyu, Gong Jianxian, Yang Zhen. Diastereoselective Construction of All-Carbon Quaternary Stereocenters via Intramolecular Oxidative Cross-Coupling Reaction[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 238-248. doi: 10.6023/cjoc201805023 shu

Diastereoselective Construction of All-Carbon Quaternary Stereocenters via Intramolecular Oxidative Cross-Coupling Reaction

Chen Wei ^a ,
Guo Renyu ^a ,
Gong Jianxian ^a,, ,
Yang Zhen ^a,b,,

a.
State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055
b.
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Beijing National Laboratory for Molecular Science(BNLMS), Peking University, Beijing 100871

Corresponding author: Gong Jianxian, zyang@pku.edu.cn Yang Zhen, gongjx@pku.edu.cn
Received Date: 10 May 2018
Revised Date: 13 September 2018
Available Online: 26 January 2018
Fund Project: the Natural Science Foundation of Guangdong Province 2016A030306011the National Natural Science Foundation of China 21632002Project supported by the National Natural Science Foundation of China (Nos. 21772008, 21632002), the Shenzhen Science and Technology Project Program (No. GRCK2017042414425972), the Natural Science Foundation of Guangdong Province (No. 2016A030306011) and the Qingdao National Laboratory for Marine Science and Technology (No. LMDBKF201703)the National Natural Science Foundation of China 21772008the Shenzhen Science and Technology Project Program GRCK2017042414425972the Qingdao National Laboratory for Marine Science and Technology LMDBKF201703

Figures(7)

The formation of sterically hindered C—C bond represents a great challenge in modern synthetic organic chemistry. A particularly challenging issue is the construction of all-carbon quaternary stereocenters. Herein, a ceric ammonium nitrate (CAN)-mediated intramolecular oxidative cross-coupling of silyl ethers for direct construction of valuable polycyclic scaffolds is described. The reaction enables sterically congested vicinal all-carbon quaternary and tertiary stereocenters to be installed diastereoselectively. The developed method provides a concise and efficient approach for ligation of two different segments through a compact C—C bond formation, which has potential applications in the synthesis of complex molecules as well as sterically congested natural products.
- oxidative coupling reaction,
- quaternary stereocenter,
- tertiary stereocenter,
- methodology
1. [1]
  For selected reviews, see: (a) Csákӱ, A. G.; Plumet, J. Chem. Soc. Rev. 2001, 30, 313.
  (b) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
  (c) Guo, F. H.; Clift, M. D.; Thomson, R. J. Eur. J. Org. Chem. 2012, 4881.
  (d) Murarka, S.; Antonchick, A. P. Synthesis 2018, 50, 2150.
2. [2]
  Ivanoff, D.; Spassoff, A. Bull. Soc. Chim. Fr. 1935, 2, 76.
3. [3]
  For selected oxidative coupling examples, see: (a) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605.
  (b) Ito, Y.; Konoike, T.; Saegusa, T. J. Am. Chem. Soc. 1975, 97, 649.
  (c) Ito, Y.; Konoike, T.; Harada, T.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 1487.
  (d) Frazier, Jr. R.; Harlow, R. J. Org. Chem. 1980, 45, 5408.
  (e) Moeller, K. D.; Tinao, L. V. J. Am. Chem. Soc. 1992, 114, 1033.
  (f) Mazzega, M.; Fabris, F.; Cossu, S.; Lucchi, O. D.; Lucchini, V.; Valle, G. Tetrahedron 1999, 55, 4427.
  (g) Jang, H. Y.; Hong, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2007, 129, 7004.
  (h) DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 11546.
  (i) Casey, B. M.; Flowers, R. A. J. Am. Chem. Soc. 2011, 133, 11492.
  (j) Amaya, T.; Maegawa, Y.; Masuda, T.; Osafune, Y.; Hirao. T. J. Am. Chem. Soc. 2015, 137, 10072.
  (k) Kaiser, D.; Teskey, C. J.; Alder, P.; Maulide. N. J. Am. Chem. Soc. 2017, 139, 16040.
  (l) Næ sborg, L.; Corti, V.; Leth, L. A.; Poulsen, P. H.; Jø rgensen. A. Angew. Chem., Int. Ed. 2018, 57, 1606.
  (m) Tanaka, T.; Tanaka, T.; Tsuji, T.; Yazaki, R.; Ohshima, T. Org. Lett. 2018, 20, 3541.
4. [4]
  For selected applications of oxidative coupling reaction in natural product synthesis, see: (a) Baran, P. S.; Guerrero, C. A.; Ambhaikar, N. B.; Hafensteiner, B. D. Angew. Chem., Int. Ed. 2005, 44, 606.
  (b) Baran, P. S.; Hafensteiner, B. D.; Ambhaikar, N. B.; Guerrero, C. A.; Gallagher, J. D. J. Am. Chem. Soc. 2006, 128, 8678.
  (c) Martin, C. L.; Overman, L. E.; Rohde, J. M. J. Am. Chem. Soc. 2008, 130, 7568.
  (d) Herzon, S. B.; Lu, L.; Woo, C. M.; Gholap, S. L. J. Am. Chem. Soc. 2011, 133, 7260.
  (e) Konkol, L. C.; Guo, F. H.; Sarjeant, A. A.; Thomson, R. J. Angew. Chem., Int. Ed. 2011, 50, 9931.
  (f) Jones, B. T.; Avetta, C. T.; Thomson, R. J. Chem. Sci. 2014, 5, 1794.
  (g) You, L.; Liang, X.-T.; Xu, L.-M.; Wang, Y.-F.; Zhang, J.-J.; Su, Q.; Li, Y.-H.; Zhang, B.; Yang, S.-L.; Chen, J.-H.; Yang, Z. J. Am. Chem. Soc. 2015, 137, 10120.
  (h) Robison, E. E.; Thomson, R. J. J. Am. Chem. Soc. 2018, 140, 1956.
5. [5]
  Wender, P. A.; Miller, B. L. In Organic Synthesis: Theory and Applications, Vol. 2, Ed.: Hudlicky, T., JAI Press, Greenwich, CT, 1993.
6. [6]
  (a) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621.
  (b) Baciocchi, E.; Casu, A.; Ruzziconi, R. Tetrahedron Lett. 1989, 30, 3707.
7. [7]
  (a) Beeson, T. D.; Mastracchio, A.; Hong, J. B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582.
  (b) Yasu, Y.; Koike, T.; Akita, M. Chem. Commun. 2012, 48, 5355.
8. [8]
  (a) Schmittel, M.; Burghart, A.; Malisch, W.; Reising, J.; Sӧllner, R. J. Org. Chem. 1998, 63, 396.
  (b) Schmittel, M.; Haeuseler, A. J. Organomet. Chem. 2002, 661, 169.
9. [9]
  (a) Avetta, C. T.; Konkol, L. C.; Taylor, C. N.; Dugan, K. C.; Stern, C. L.; Thomson, R. J. Org. Lett. 2008, 10, 5621.
  (b) Konkol, L. C.; Jones, B. T.; Thomson, R. J. Org. Lett. 2009, 11, 5550.
10. [10]
  (a) Fuji, K. Chem. Rev. 1993, 93, 2037.
  (b) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
  (c) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591.
  (d) Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5363.
  (e) Christoffers, J.; Baro, A. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis, Wiley-VCH, Weinheim, 2005.
  (f) Trost, B. M.; Jiang, C. Synthesis 2006, 369.
  (g) Hawner. C.; Alexakis, A. Chem. Commun. 2010, 46, 7295.
  (h) Shimizu, M. Angew. Chem., Int. Ed. 2011, 50, 5998.
  (i) Hong, A. Y.; Stoltz, B. M. Eur. J. Org. Chem. 2013, 2745.
  (j) Quasdorf, K. W.; Overman, L. E. Nature 2014, 516, 181.
  (k) Long, R.; Huang, J.; Gong, J. X.; Yang, Z. Nat. Prod. Rep. 2015, 32, 1584.
11. [11]
  (a) Arya, P.; Joseph, R.; Chou, D. T. H. Chem. Biol. 2002, 9, 145.
  (b) Juncosa Jr, J. I.; Hansen, M.; Bonner, L. A.; Cueva, J. P.; Maglathlin, R.; McCorvy, J. D.; Marona-Lewicka, D.; Lill, M. A.; Nichols, D. E. ACS Chem. Neurosci. 2013, 4, 96.
12. [12]
  (a) Narayanan, C. R.; Pachapurkar, R. V. Tetrahedron Lett. 1965, 48, 4333.
  (b) Ziffer, H.; Weiss, U.; Narayanan, C. R.; Pachapurkar, R. V. J. Org. Chem. 1966, 31, 2691.
  (c) Harris, M.; Henderson, R.; McCrindle, R.; Overton, K. H.; Turner, D. W. Tetrahedron 1968, 24, 1517.
13. [13]
  Fontana, A.; Muniain, C.; Cimino, G. J. Nat. Prod. 1998, 61, 1027. doi: 10.1021/np980073k
14. [14]
  Gonzalez, M. Curr. Bioact. Compd. 2007, 3, 1. doi: 10.2174/157340707780126534
15. [15]
  (a) Zhang, P. P.; Yan, Z. M.; Li, Y. H.; Gong, G. X.; Yang, Z. J. Am. Chem. Soc. 2017, 139, 13989.
  (b) Huang, J.; Gu, Y. Q.; Guo, K.; Zhu, L.; Lan, Y.; Gong, G. X.; Yang, Z. Angew. Chem., Int. Ed. 2017, 56, 7890.
  (c) Liu, D.-D.; Sun, T.-W.; Wang, K.-Y.; Lu, Y.; Zhang, S.-L.; Li, Y.-H.; Jiang, Y.-L.; Chen, J.-H.; Yang, Z. J. Am. Chem. Soc. 2017, 139, 5732.
  (d) Huang, Z. H.; Huang, J.; Qu, Y. Z.; Zhang, W. B.; Gong, J. X.; Yang, Z. Angew. Chem., Int. Ed. 2018, 57, 8744.
16. [16]
  Paquette, L. A.; Bzowej, E. I.; Branan, B. M.; Stanton, K. J. J. Org. Chem. 1995, 60, 7277. doi: 10.1021/jo00127a037
17. [17]
  (a) Dessau, R. M.; Heiba, E. I. J. Org. Chem. 1974, 39, 3457.
  (b) Liu, X. G.; Chen, X. H.; Mohr, J. T. Org. Lett. 2016, 18, 3182.
18. [18]
  Kobayashi, Y.; Taguchi, T.; Tokuno, E. Tetrahedron Lett. 1977, 3741.
19. [19]
  CDCC 1501822(15), CDCC 1582641(30) and CDCC 1861685(32) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, U. K.; fax: +44-1223336033.
20. [20]
  (a) Chatgilialoglu, C.; Studer, A. Encyclopedia of Radicals in Chemistry, Biology and Materials, Vols. 1~4, Wiley, Chichester, 2012.
  (b) Zhang, N.; Samanta, S. R.; Rosen, B. M.; Percec, V. Chem. Rev. 2014, 114, 5848.
  (c) Studer, A.; Curran, D. P. Angew. Chem., Int. Ed. 2016, 55, 58.
  (d) Zard, S. Z. Org. Lett. 2017, 19, 1257.
21. [21]
  Frazier, Jr. R.; Harlow, R. J. Org. Chem. 1980, 45, 5408. doi: 10.1021/jo01314a052
22. [22]
  (a) Schmittel, M.; Sӧllner, R. Chem. Ber./Rec. 1997, 130, 771.
  (b) Schmittel, M.; Burghart, A.; Werner, H.; Laubender, M.; Sӧllner, R. J. Org. Chem. 1999, 104, 3077.
1. [1]
  Xue-Peng Zhang , Yuchi Long , Yushu Pan , Jiding Wang , Baoyu Bai , Rui Ding . 定量构效关系方法学习探索：以钴卟啉活化氧气为例. University Chemistry, 2025, 40(8): 345-359. doi: 10.12461/PKU.DXHX202410107
2. [2]
  Yueguang Chen , Wenqiang Sun . “Carbon” Adventures. University Chemistry, 2024, 39(9): 248-253. doi: 10.3866/PKU.DXHX202308074
3. [3]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
4. [4]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
5. [5]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
6. [6]
  Kai CHEN , Fengshun WU , Shun XIAO , Jinbao ZHANG , Lihua ZHU . PtRu/nitrogen-doped carbon for electrocatalytic methanol oxidation and hydrogen evolution by water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1357-1367. doi: 10.11862/CJIC.20230350
7. [7]
  Zhonghan Xu , Yuejia Li , Kin Shing Chan . 碳中和新旅程. University Chemistry, 2025, 40(6): 167-171. doi: 10.12461/PKU.DXHX202407075
8. [8]
  Zixuan Zhao , Miao Fan . “Carbon” with No “Ester”: A Boundless Journey of CO₂ Transformation. University Chemistry, 2025, 40(7): 213-217. doi: 10.12461/PKU.DXHX202409040
9. [9]
  Xuzhen Wang , Xinkui Wang , Dongxu Tian , Wei Liu . Enhancing the Comprehensive Quality and Innovation Abilities of Graduate Students through a “Student-Centered, Dual Integration and Dual Drive” Teaching Model: A Case Study in the Course of Chemical Reaction Kinetics. University Chemistry, 2024, 39(6): 160-165. doi: 10.3866/PKU.DXHX202401074
10. [10]
  Lei Shu , Zimin Duan , Yushen Kang , Zijian Zhao , Hong Wang , Lihua Zhu , Hui Xiong , Nan Wang . An Exploration of the CO₂-Involved Carbon Cycle World. University Chemistry, 2024, 39(5): 144-153. doi: 10.3866/PKU.DXHX202309084
11. [11]
  Yuting Zhang , Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037
12. [12]
  Wuxin Bai , Qianqian Zhou , Zhenjie Lu , Ye Song , Yongsheng Fu . Co-Ni Bimetallic Zeolitic Imidazolate Frameworks Supported on Carbon Cloth as Free-Standing Electrode for Highly Efficient Oxygen Evolution. Acta Physico-Chimica Sinica, 2024, 40(3): 2305041-0. doi: 10.3866/PKU.WHXB202305041
13. [13]
  Xiaomei Ning , Liang Zhan , Xiaosong Zhou , Jin Luo , Xunfu Zhou , Cuifen Luo . Preparation and Electro-Oxidation Performance of PtBi Supported on Carbon Cloth: A Recommended Comprehensive Chemical Experiment. University Chemistry, 2024, 39(11): 217-224. doi: 10.3866/PKU.DXHX202401085
14. [14]
  Kaihui Huang , Dejun Chen , Xin Zhang , Rongchen Shen , Peng Zhang , Difa Xu , Xin Li . Constructing Covalent Triazine Frameworks/N-Doped Carbon-Coated Cu₂O S-Scheme Heterojunctions for Boosting Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(12): 2407020-0. doi: 10.3866/PKU.WHXB202407020
15. [15]
  Wenhui Li , Yakun Tang , Yusheng Zhou , Yue Zhang , Wenhai Zhang , Qingtao Ma , Lang Liu , Sen Dong , Yuliang Cao . Enhanced sodium storage performance of asphalt-derived hard carbon through intramolecular oxidation for high-performance sodium-ion batteries. Acta Physico-Chimica Sinica, 2025, 41(10): 100119-0. doi: 10.1016/j.actphy.2025.100119
16. [16]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
17. [17]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
18. [18]
  Lei Shu , Zhengqing Hao , Kai Yan , Hong Wang , Lihua Zhu , Fang Chen , Nan Wang . Development of a Double-Carbon Related Experiment: Preparation, Characterization and Carbon-Capture Ability of Eggshell-Derived CaO. University Chemistry, 2024, 39(4): 149-156. doi: 10.3866/PKU.DXHX202310134
19. [19]
  Haoran Zhang , Yaxin Jin , Peng Kang , Sheng Zhang . The Convergence and Innovative Application of Artificial Intelligence in Scientific Research: A Case Study of Electrocatalytic Carbon Dioxide Reduction in the Context of the Dual-Carbon Strategy. University Chemistry, 2025, 40(9): 148-155. doi: 10.12461/PKU.DXHX202412099
20. [20]
  Wenli FENG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress on ultralong room temperature phosphorescent carbon dots. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 833-846. doi: 10.11862/CJIC.20240308

Get Citation

PDF

XML

Metrics

PDF Downloads(30)
Abstract views(2210)
HTML views(438)

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