Citation: Zhu Chaoze, Feng Jianjun, Zhang Junliang. Rhodium(Ⅰ)-Catalyzed Stereospecific [3+2] Cycloadditions of Vinylaziridines and Ynamides[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1165-1172. doi: 10.6023/cjoc201701043 shu

Rhodium(Ⅰ)-Catalyzed Stereospecific [3+2] Cycloadditions of Vinylaziridines and Ynamides

Zhu Chaoze ^a ,
Feng Jianjun ^a,*,, ,
Zhang Junliang ^a,*,,

a.
School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062

Corresponding author: Feng Jianjun, jjfeng@chem.ecnu.edu.cn Zhang Junliang, jlzhang@chem.ecnu.edu.cn
Received Date: 21 January 2017
Revised Date: 16 February 2017

Fund Project: the National Natural Science Foundation of China 21373088by the Shanghai Sailing Program 15YF1403600the National Natural Science Foundation of China 21602062the National Natural Science Foundation of China 21425205

Figures(3)

The first rhodium-catalyzed stereospecific intermolecular [3+2] cycloaddition reaction of vinylaziridines with ynamides was realized. The salient features of the transformation include broad substrate scope, mild reaction condition, and simple operation. Moreover, the chirality of vinylaziridines can be completely transferred to the cycloadducts, representing an atom-economic and enantiospecific protocol for the construction of valuable 2-amino pyrroline derivatives.
- transition-metal catalysis,
- cycloaddition,
- vinylaziridine,
- ynamides,
- nitrogen heterocycles
1. [1]
2. [2]
  (a) Cheng, M.; Li, Q.; Lin, B.; Sha, Y.; Ren, J.; He, Y.; Wang, Q.; Hua, H.; Ruud, K. Tetrahedron: Asymmetry 2006, 17, 179. (b) Bugni, T. S.; Woolery, M.; Kauffman, C. A.; Jensen, P. P.; Fenical, W. J. Nat. Prod. 2006, 69, 1626. (c) Fu, P.; La, S.; MacMillan, J. B. J. Nat. Prod. 2016, 79, 455. (d) Fu, P.; Legako, A.; La, S.; MacMillan, J. B. Chem. Eur. J. 2016, 22, 3491.
3. [3]
  (a) Zhou, A.-H.; He, Q.; Shu, C.; Yu, Y.-F.; Liu, S.; Zhao T.; Zhang, W.; Lu, X.; Ye, L.-W. Chem. Sci. 2015, 6, 1265. (b) Xiao, X.-Y.; Zhou, A.-H.; Shu, C.; Pan, F.; Li T.; Ye, L.-W. Chem. Asian J. 2015, 10, 1854. (c) Yu, W.; Chen, W.; Liu, S.; Shao, J.; Shao, Z.; Lin, H.; Yu, Y. Tetrahedron 2013, 69, 1953. (d) Wang, W.; Xu, X.-P; Wang, S.-Y.; Zhou, W.; Ji, S.-J. Org. Lett. 2013, 15, 4246. (e) Qi, X.; Xiang, H.; He, Q.; Yang, C. Org. Lett. 2014, 16, 4186. (f) Fontaine, P.; Masson, G.; Zhu, J. Org. Lett. 2009, 11, 1555.
4. [4]
  (a) Ghorai, M. K.; Tiwari, D. P. J. Org. Chem. 2013, 78, 2617. (b) Tsuge, O.; Hatta, T.; Tashiro, H.; Kakura, Y.; Maeda, H.; Kakehi, A. Tetrahedron 2000, 56, 7723. (c) Nestorak, I. Y.; Tverdokhlebov, A. V.; Tolmachev, A. A.; Volovenko, Y. M. Heterocycles 2010, 81, 611. (d) Duvall, J. R.; Wu, F.; Snider, B. B. J. Org. Chem. 2006, 71, 8579. (e) Stevens, K.; Tyrrell, A. J.; Skerratt, S.; Robertson, J. Org. Lett. 2011, 13, 5964.
5. [5]
6. [6]
  (a) Wang, X.-N.; Yeom, H.-S.; Fang, L.-C.; He, S.; Ma, Z.-X.; Kedrowski, B. L.; Hsung, R. P. Acc. Chem. Res. 2014, 47, 560. (b) Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., Int. Ed. 2010, 49, 2840. (c) DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064. (d) Pawar, S. K.; Vasu, D.; Liu, R.-S. Adv. Synth. Catal. 2014, 356, 2411. (e) Singh, R. K. R.; Pawar, S. K.; Huang, M.-J.; Liu, R.-S. Chem. Commun. 2016, 52, 11434. (f) Liu, J.; Chen, M.; Zhang, L.; Liu, Y. Chem. Eur. J. 2015, 21, 1009.
7. [7]
  (a) Mackay, W. D.; Fistikci, M.; Carris, R. M.; Johnson, J. S. Org. Lett. 2014, 16, 1626. (b) Movassaghi, M.; Jacobsen, E. N. J. Am. Chem., Soc. 2002, 124, 2456. (c) Karad, S. N.; Bhunia, S.; Liu, R.-S. Angew. Chem., Int. Ed. 2012, 51, 8722.
8. [8]
  (a) Feng, J.-J.; Lin, T.-Y.; Zhu, C.-Z.; Wang, H.; Wu, H.-H.; Zhang, J. J. Am. Chem. Soc. 2016, 138, 2178. (b) Lin, T.-Y.; Zhu, C.-Z.; Zhang, P.; Wang, Y.; Wu, H.-H.; Feng, J.-J.; Zhang, J. Angew. Chem., Int. Ed. 2016, 55, 10844. (c) Zhu, C.-Z.; Feng, J.-J.; Zhang, J. Angew. Chem., Int. Ed. 2017, 56, 1351. (d) Feng, J.-J.; Lin, T.-Y.; Zhu, C.-Z.; Wang, H.; Wu, H.-H.; Zhang, J. J. Am. Chem. Soc. 2015, 137, 3787. (e) Feng, J.-J.; Lin, T.-Y.; Wu, H.-H.; Zhang, J. Angew. Chem., Int. Ed. 2015, 54, 15854.
9. [9]
  (a) Wender, P. A.; Strand, D. J. Am. Chem. Soc. 2009, 131, 7528. (b) Fan, J.; Gao, L.; Wang, Z. Chem. Commun. 2009, 5021. (c) Xu, C.-F.; Zheng, B.-H.; Suo, J.-J.; Ding, C.-H.; Hou, X.-L. Angew. Chem., Int. Ed. 2015, 54, 1604. (d) Hou, X.-L.; Wu, J.; Fan, R.-H.; Ding, C.-H.; Luo, Z.-B.; Dai, L.-X. Synlett 2006, 181.
10. [10]
  Zhang, X. Zou, H. Huang, G. ChemCatChem 2016, 8, 2549. doi: 10.1002/cctc.201600349
11. [11]
  (a) Wender, P. A.; Williams, T. J. Angew. Chem., Int. Ed. 2002, 41, 4550. (b) Mansfield, S. J.; Campbell, C. D.; Jones, M. W.; Anderson, E. A. Chem. Commun. 2015, 51, 3316.
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