Highly efficient and diastereoselective construction of substituted pyrrolidines bearing a quaternary carbon center via 1,3-dipolar cycloaddition
Kai-Kai Wang
School of Pharmacy, Key Laboratory of Nano-carbon Modified Film Technology Engineering of Henan Province, Xinxiang University, Xinxiang, China
Search for more papers by this authorYan-Li Li
Medical College, Xinxiang University, Xinxiang, China
Search for more papers by this authorXiao-Qian Shuai
Xinxiang Science and Technology Association, Xinxiang, China
Search for more papers by this authorCorresponding Author
Rongxiang Chen
School of Pharmacy, Key Laboratory of Nano-carbon Modified Film Technology Engineering of Henan Province, Xinxiang University, Xinxiang, China
Correspondence
Rongxiang Chen and Zhan-Yong Wang, School of Pharmacy, Xinxiang University, Xinxiang 453000, China.
Email: [email protected] (R. C.) and [email protected] (Z.-Y. W.)
Search for more papers by this authorAili Sun
School of Pharmacy, Key Laboratory of Nano-carbon Modified Film Technology Engineering of Henan Province, Xinxiang University, Xinxiang, China
Search for more papers by this authorCorresponding Author
Zhan-Yong Wang
School of Pharmacy, Key Laboratory of Nano-carbon Modified Film Technology Engineering of Henan Province, Xinxiang University, Xinxiang, China
Correspondence
Rongxiang Chen and Zhan-Yong Wang, School of Pharmacy, Xinxiang University, Xinxiang 453000, China.
Email: [email protected] (R. C.) and [email protected] (Z.-Y. W.)
Search for more papers by this authorKai-Kai Wang
School of Pharmacy, Key Laboratory of Nano-carbon Modified Film Technology Engineering of Henan Province, Xinxiang University, Xinxiang, China
Search for more papers by this authorYan-Li Li
Medical College, Xinxiang University, Xinxiang, China
Search for more papers by this authorXiao-Qian Shuai
Xinxiang Science and Technology Association, Xinxiang, China
Search for more papers by this authorCorresponding Author
Rongxiang Chen
School of Pharmacy, Key Laboratory of Nano-carbon Modified Film Technology Engineering of Henan Province, Xinxiang University, Xinxiang, China
Correspondence
Rongxiang Chen and Zhan-Yong Wang, School of Pharmacy, Xinxiang University, Xinxiang 453000, China.
Email: [email protected] (R. C.) and [email protected] (Z.-Y. W.)
Search for more papers by this authorAili Sun
School of Pharmacy, Key Laboratory of Nano-carbon Modified Film Technology Engineering of Henan Province, Xinxiang University, Xinxiang, China
Search for more papers by this authorCorresponding Author
Zhan-Yong Wang
School of Pharmacy, Key Laboratory of Nano-carbon Modified Film Technology Engineering of Henan Province, Xinxiang University, Xinxiang, China
Correspondence
Rongxiang Chen and Zhan-Yong Wang, School of Pharmacy, Xinxiang University, Xinxiang 453000, China.
Email: [email protected] (R. C.) and [email protected] (Z.-Y. W.)
Search for more papers by this authorFunding information: Key Scientific and Technological Project of Xinxiang, Grant/Award Number: 21ZD010; National College Students Innovation and Entrepreneurship Training Program, Grant/Award Numbers: 202111071021, 202111071025; Key Scientific Research Project of Colleges and Universities in Henan Province, Grant/Award Numbers: 22B150015, 20B150019, 18A150014; Natural Science Foundation of Henan Province, Grant/Award Number: 202300410016; Program for Youth Backbone Teacher Training at the University of Henan Province, Grant/Award Number: 2021GGJS163; National Natural Science Foundation of China, Grant/Award Number: 21801214
Abstract
A general approach to substituted pyrrolidines via [3 + 2] cycloaddition between nonstabilized azomethine ylides and cyanosulfones was developed. The efficient method provides a series of substituted pyrrolidines bearing a quaternary carbon center in high yields (up to 98%) excellent diastereoselectivities (up to >25:1 dr) under ambient reaction conditions.
Open Research
DATA AVAILABILITY STATEMENT
The data that supports the findings of this study are available in the supplementary material of this article.
Supporting Information
| Filename | Description |
|---|---|
| jhet4494-sup-0001-DataS1.docWord document, 14.3 MB | Data S1 Supporting information. |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1M. J. Meyers, J. Liu, Z. Liu, H. Ma, L. Dai, D. Adah, S. Zhao, X. Li, X. Liu, Y. Lu, Y. Huang, Z. Tu, X. Chen, M. D. Tortorella, ACS. Med. Chem. Lett. 2019, 10, 966.
- 2J. Li, Y. Ye, Y. Zhang, Org. Chem. Front. 2018, 5, 864.
- 3F. An, B. Maji, E. Min, A. R. Ofial, H. Mayr, J. Am. Chem. Soc. 2020, 142, 1526.
- 4D. T. Thu Huong, M.-T. Martin, M. Litaudon, T. Sévenet, M. Païs, J. Nat. Prod. 1998, 61, 1444.
- 5X. Cheng, D. Yan, X.-Q. Dong, C.-J. Wang, Asian J. Org. Chem. 2020, 9, 1567.
- 6E. M. Buev, A. A. Smorodina, V. S. Moshkin, V. Y. Sosnovskikh, Tetrahedron Lett. 2019, 60, 649.
- 7Y. Yamaberi, R. Eto, T. Umeno, T. Kato, M. Doi, H. Yokoo, M. Oba, M. Tanaka, Org. Lett. 2021, 23, 4358.
- 8C.-Z. Zhu, J.-J. Feng, J. Zhang, Chem. Commun. 2018, 54, 2401.
- 9J. J. W. Duan, Z. Lu, B. Jiang, S. Stachura, C. A. Weigelt, J. S. Sack, J. Khan, M. Ruzanov, M. A. Galella, D.-R. Wu, M. Yarde, D.-R. Shen, D. J. Shuster, V. Borowski, J. H. Xie, L. Zhang, S. Vanteru, A. K. Gupta, A. Mathur, Q. Zhao, W. Foster, L. M. Salter-Cid, P. H. Carter, T. G. M. Dhar, ACS. Med. Chem. Lett. 2019, 10, 367.
- 10G. Pandey, P. Banerjee, S. R. Gadre, Chem. Rev. 2006, 106, 4484.
- 11R. Narayan, M. Potowski, Z.-J. Jia, A. P. Antonchick, H. Wadmann, Acc. Chem. Res. 2014, 47, 1296.
- 12B. Bdiri, B.-J. Zhao, Z.-M. Zhou, Tetrahedron: Asymmetry 2017, 28, 876.
- 13M. S. Singh, S. Chowdhury, S. Koley, Tetrahedron 2016, 72, 1603.
- 14X. Fang, C.-J. Wang, Org. Biomol. Chem. 2018, 16, 2591.
- 15E. M. Buev, V. S. Moshkin, V. Y. Sosnovskikh, Org. Lett. 2016, 18, 1764.
- 16V. I. Savych, V. L. Mykhalchuk, P. V. Melnychuk, A. O. Isakov, T. Savchuk, V. M. Timoshenko, S. A. Siry, S. O. Pavlenko, D. V. Kovalenko, O. V. Hryshchuk, V. A. Reznik, B. A. Chalyk, V. S. Yarmolchuk, E. B. Rusanov, P. K. Mykhailiuk, J. Org. Chem. 2021, 86, 13289.
- 17D. L. Obydennov, V. D. Steben'kov, K. L. Obydennov, S. A. Usachev, V. S. Moshkin, V. Y. Sosnovskikh, Synthesis 2021, 53, 2621.
- 18E. M. Buev, M. A. Stepanov, V. S. Moshkin, V. Y. Sosnovskikh, Org. Lett. 2020, 22, 631.
- 19S. Zimmermann, M. Akbarzadeh, F. Otte, C. Strohmann, M. G. Sankar, S. Ziegler, A. Pahl, S. Sievers, K. Kumar, Chem. Eur. J. 2019, 25, 15498.
- 20K.-K. Wang, Y.-L. Li, G.-Y. Ma, M.-H. Yi, B.-K. Zhu, J. Heterocyclic Chem. 2019, 56, 2274.
- 21T. Thierry, C. Lebargy, E. Pfund, T. Lequeux, J. Org. Chem. 2019, 84, 5877.
- 22J. K. Laha, K. P. Jethava, J. Org. Chem. 2017, 82, 3597.
- 23E. M. Buev, V. S. Moshkin, V. Y. Sosnovskikh, J. Org. Chem. 2017, 82, 12827.
- 24C. Izquierdo, F. Esteban, J. L. G. Ruano, A. Fraile, J. Alemán, Org. Lett. 2016, 18, 92.
- 25B. A. Chalyk, A. A. Isakov, M. V. Butko, K. V. Hrebeniuk, O. V. Savych, O. V. Kucher, K. S. Gavrilenko, T. V. Druzhenko, V. S. Yarmolchuk, S. Zozulya, P. K. Mykhailiuk, Eur. J. Org. Chem. 2017, 2017, 4530.
- 26V. L. Mykhalchuk, V. S. Yarmolchuk, R. O. Doroschuk, A. A. Tolmachev, O. O. Grygorenko, Eur. J. Org. Chem. 2018, 2018, 2870.
- 27K.-K. Wang, Y.-L. Li, Z.-Y. Wang, M.-W. Hu, T.-T. Qiu, B.-K. Zhu, Org. Biomol. Chem. 2019, 17, 244.
- 28S.-N. Li, B. Yu, J. Liu, H.-L. Li, R. Na, Synlett 2016, 27, 282.
- 29M. Beuvin, M. Manneveau, S. Diab, B. Picard, M. Sanselme, S. R. Piettre, J. Legros, I. Chataigner, Tetrahedron Lett. 2018, 59, 4487.
- 30M. Manneveau, S. Tanii, F. Gens, J. Legros, I. Chataigner, Org. Biomol. Chem. 2020, 18, 3481.
- 31S. Pimparkar, A. Koodan, S. Maiti, N. S. Ahmed, M. M. M. Mostafa, D. Maiti, Chem. Commun. 2021, 57, 2210.
- 32J. Schörgenhumer, M. Waser, Org. Chem. Front. 2016, 3, 1535.
- 33K. Ohmatsu, Y. Morita, M. Kiyokawa, T. Ooi, J. Am. Chem. Soc. 2021, 143, 11218.
- 34T. Cui, Y. Zhan, C. Dai, J. Lin, P. Liu, P. Sun, J. Org. Chem. 2021, 86, 15897.
- 35X. Hu, Q. Bian, Z.-L. Wang, L.-J. Guo, Y.-Z. Xu, G. Wang, D.-Z. Xu, J. Org. Chem. 2022, 87, 66.
- 36Z.-Q. Xu, W.-B. Wang, L.-C. Zheng, L. Li, L. Duan, Y.-M. Li, Org. Biomol. Chem. 2019, 17, 9026.
- 37J. Aziz, S. Messaoudi, M. Alami, A. Hamze, Org. Biomol. Chem. 2014, 12, 9743.
- 38Y. Fang, Z. Luo, X. Xu, RSC Adv. 2016, 6, 59661.
- 39X. Chen, S. Hussain, S. Parveen, S. Zhang, Y. Yang, C. Zhu, Curr. Med. Chem. 2012, 19, 3578.
- 40S. Rajkumar, K. Shankland, J. M. Goodman, A. J. A. Cobb, Org. Lett. 2013, 15, 1386.
- 41L. S. Aitken, L. E. Hammond, R. Sundaram, K. Shankland, G. D. Brown, A. J. A. Cobb, Chem. Commun. 2015, 51, 13558.
