RSS-Feed abonnieren
DOI: 10.1055/a-1878-8084
Construction of Quaternary Allylic Amino Acid Derivatives through Palladium-Catalyzed Allylic Alkylation Reaction of Azlactones with Vinyl Aziridine
Autor*innen
We are grateful for the financial support from Youth Foundation of Henan Scientific Committee (No. 222300420249), Foundation of Henan Education Committee (No. 21A150039) and Doctoral Research Start-up Fund project of Nanyang Institute of Technology (No. NGBJ-2021-03).

Abstract
A highly efficient Pd-catalyzed allylic alkylation reaction of azlactones with vinyl aziridine has been achieved for the first time to access functionalized quaternary allylic amino acid derivatives (17 examples, up to 89% yield and 80% ee). Moreover, the broad scope and easy transformations of the products reinforce the value of this approach, which can enrich the chemistry of quaternary allylic amino acid derivatives.
Key words
allylic alkylation - quaternary allylic amino acid derivatives - Pd-catalyzed - vinyl aziridine - azlactonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1878-8084.
- Supporting Information (PDF) (opens in new window)
Publikationsverlauf
Eingereicht: 15. April 2022
Angenommen nach Revision: 20. Juni 2022
Accepted Manuscript online:
20. Juni 2022
Artikel online veröffentlicht:
27. Juli 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Venkatraman J, Shankaramma SC, Balaram P. Chem. Rev. 2001; 101: 3131
- 2 Liu WX, Wang R. Med. Res. Rev. 2012; 32: 536
- 3a Nájera C, Sansano JM. Chem. Rev. 2007; 107: 4584
- 3b Hyslop JF, Lovelock SL, Sutton PW, Brown KK, Watson AJ. B, Roiban G.-D. Angew. Chem. Int. Ed. 2018; 57: 13821
- 3c Cativiela C, Ordóňez M, Viveros-Ceballos JL. Tetrahedron 2020; 76: 130875
- 4a Fisk JS, Mosey RA, Tepe JJ. Chem. Soc. Rev. 2007; 36: 1432
- 4b de Castro PP, Carpanez AG, Amarante GW. Chem. Eur. J. 2016; 22: 10294
- 4c Ma C, Zhou J.-Y, Zhang Y.-Z, Mei G.-J, Shi F. Angew. Chem. Int. Ed. 2018; 57: 5398
- 4d Marra IF. S, de Castro PP, Amarante GW. Eur. J. Org. Chem. 2019; 5830
- 5a Cabrera S, Reyes E, Alemán J, Milelli A, Kobbelgaard S, Jørgensen KA. J. Am. Chem. Soc. 2008; 130: 12031
- 5b Terada M, Tanaka H, Sorimachi K. J. Am. Chem. Soc. 2009; 131: 3430
- 5c Terada M, Moriya K, Kanomata K, Sorimachi K. Angew. Chem. Int. Ed. 2011; 50: 12586
- 5d Zhou H, Yang H, Liu M, Xia C, Jiang G. Org. Lett. 2014; 16: 5350
- 5e Zhang J, Liu X, Wu C, Zhang P, Chen J, Wang R. Eur. J. Org. Chem. 2014; 7104
- 5f Kalek M, Fu GC. J. Am. Chem. Soc. 2015; 137: 9438
- 5g Wei X, Liu D, An Q, Zhang W. Org. Lett. 2015; 17: 5768
- 5h Wang T, Yu Z, Hoon DL, Phee CY, Lan Y, Lu Y. J. Am. Chem. Soc. 2016; 138: 265
- 5i Yoshioka K, Yamada K, Uraguchi D, Ooi T. Chem. Commun. 2017; 53: 5495
- 5j Zhang L, Han Y, Huang A, Zhang P, Li P, Li W. Org. Lett. 2019; 21: 7415
- 5k Zhang Z, Xiao F, Wu H.-M, Dong X.-Q, Wang C.-J. Org. Lett. 2020; 22: 569
- 6a Lu G, Birman VB. Org. Lett. 2011; 13: 356
- 6b Wang C, Luo H.-W, Gong L.-Z. Synlett 2011; 992
- 6c Rodríguez-Docampo Z, Quigley C, Tallon S, Connon SJ. J. Org. Chem. 2012; 77: 2407
- 6d Palacio C, Connon SJ. Eur. J. Org. Chem. 2013; 5398
- 6e Yu K, Liu X, Lin X, Lin L, Feng X. Chem. Commun. 2015; 51: 14897
- 6f Tallon S, Manoni F, Connon SJ. Angew. Chem. Int. Ed. 2015; 54: 813
- 6g Zhang Y.-C, Yang Q, Yang X, Zhu Q.-N, Shi F. Asian J. Org. Chem. 2016; 5: 914
- 6h Mandai H, Hongo K, Fujiwara T, Fujii K, Mitsudo K, Suga S. Org. Lett. 2018; 20: 4811
- 6i Xie M.-S, Huang B, Li N, Tian Y, Wu X.-X, Deng Y, Qu G.-R, Guo H.-M. J. Am. Chem. Soc. 2020; 142: 19226
- 7a Dong S, Liu X, Zhu Y, He P, Lin L, Feng X. J. Am. Chem. Soc. 2013; 135: 10026
- 7b Liu X, Wang Y, Yang D, Zhang J, Liu D, Su W. Angew. Chem. Int. Ed. 2016; 55: 8100
- 7c Yu X.-Y, Chen J.-R, Wei Q, Cheng H.-G, Liu Z.-C, Xiao W.-J. Chem. Eur. J. 2016; 22: 6774
- 7d Zhang S.-Y, Lv M, Yin S.-J, Li N.-K, Zhang J.-Q, Wang X.-W. Adv. Synth. Catal. 2016; 358: 143
- 7e Zhang L, Liu Y, Liu K, Liu Z, He N, Li W. Org. Biomol. Chem. 2017; 15: 8743
- 7f Zhou J, Wang M.-L, Gao X, Jiang G.-F, Zhou Y.-G. Chem. Commun. 2017; 53: 3531
- 7g Ruan S, Lin X, Xie L, Lin L, Feng X, Liu X. Org. Chem. Front. 2018; 5: 32
- 7h Lin X, Fang F, Lin W, Liu Z, Chang X, Li P, Li W. Asian. J. Org. Chem. 2020; 9: 1187
- 7i Yuan W.-C, Quan B.-X, Zhao J.-Q, You Y, Wang Z.-H, Zhou M.-Q. J. Org. Chem. 2020; 85: 11812
- 7j Xie L, Li Y, Dong S, Feng X, Liu X. Chem. Commun. 2021; 57: 239
- 8a Zhao H.-W, Ding W.-Q, Wang L.-R, Guo J.-M, Song X.-Q, Wu H.-H, Tang Z, Fan X.-Z, Bi X.-F. Eur. J. Org. Chem. 2020; 5557
- 8b Liu Z, Feng X, Xu J, Jiang X, Cai X. Tetrahedron Lett. 2020; 61: 151694
- 9a Feng J.-J, Zhang J. ACS Catal. 2016; 6: 6651
- 9b Rivinoja DJ, Gee YS, Gardiner MG, Ryan JH, Hyland CJ. T. ACS Catal. 2017; 7: 1053
- 9c Gao J, Zhang J, Fang S, Feng J, Lu T, Du D. Org. Lett. 2020; 22: 7725
- 9d Drew MA, Tague AJ, Richardson C, Pyne SG, Hyland CJ. T. Org. Lett. 2021; 23: 4635
- 9e Niu B, Wei Y, Shi M. Org. Chem. Front. 2021; 8: 3475
- 9f Xiao S, Chen B, Jiang Q, He L, Chu W.-D, He C.-Y, Liu Q.-Z. Org. Chem. Front. 2021; 8: 3729
- 10a Trost BM, Fandrick DR, Brodmann T, Stiles DT. Angew. Chem. Int. Ed. 2007; 46: 6123
- 10b Ohno H. Chem. Rev. 2014; 114: 7784
- 10c Zhuo C.-X, Zheng C, You S.-L. Acc. Chem. Res. 2014; 47: 2558
- 10d Lin T.-Y, Wu H.-H, Feng J.-J, Zhang J. ACS Catal. 2017; 7: 4047
- 10e Lin T.-Y, Wu H.-H, Feng J.-J, Zhang J. Org. Lett. 2017; 19: 2897
- 10f Pham QH, Tague AJ, Richardson C, Hyland CJ. T, Pyne SG. Chem. Sci. 2021; 12: 12695
- 10g Pàmies O, Margalef J, Cañellas S, James J, Judge E, Guiry PJ, Moberg C, Bäckvall J.-E, Pfaltz A, Pericàs MA, Diéguez M. Chem. Rev. 2021; 121: 4373
For some recent examples:
For some examples, see:
For some recent examples, see:
For some recent examples, see: