Recent progress in the synthesis of functionalized β-lactams through transition-metal-catalyzed C(sp3)-H amidation

Synlett

Volumn 25, Issue 14, 2014, Pages 1941-1945

  Zhang, Qi ^a   Chen, Kai ^a   Shi, Bing Feng ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

amidation; copper; directing groups; palladium; lactams

Indexed keywords

8 AMINOQUINOLINE DERIVATIVE; ALPHA AMINO BETA LACTAM; AMIDE; BETA LACTAM DERIVATIVE; COPPER; PALLADIUM; UNCLASSIFIED DRUG;

AMIDATION; AMINATION; ARTICLE; ARYLATION; CARBON HYDROGEN FUNCTIONALIZATION; CATALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; STEREOCHEMISTRY;

EID: 84906791172     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0033-1338645     Document Type: Article

References (35)

1. Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B.; Gorman, M., Eds.; Academic Press: New York, 1982.
2. Kamath, A.; Ojima, I. Tetrahedron 2012, 68, 10640.
3. Böttcher, T.; Sieber, S. A. Med. Chem. Commun. 2012, 3, 408.
4. For selected reviews, see: France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. Acc. Chem. Res. 2004, 37, 592.
5. Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Curr. Med. Chem. 2004, 11, 1837.
6. For selected reviews, see: Mei, T.-S.; Kou, L.; Ma, S.; Engle, K. M.; Yu, J.-Q. Synthesis 2012, 44, 1778.
7. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068.
8. Thansandote, P.; Lautens, M. Chem. Eur. J. 2009, 15, 5874.
9. Neumann, J. J.; Rakshit, S.; Dröge, T.; Glorius, F. Angew. Chem. Int. Ed. 2009, 48, 6892.
10. He, G.; Zhao, Y.; Zhang, S.; Lu, C.; Chen, G. J. Am. Chem. Soc. 2012, 134, 3.
11. Nadres, E. T.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 7.
12. He, G.; Zhang, S.-Y.; Nack, W. A.; Li, Q.; Chen, G. Angew. Chem. Int. Ed. 2013, 52, 11124.
13. Ye, X.; He, Z.; Ahmed, T.; Weise, K.; Akhmedov, N. G.; Petersen, J. L.; Shi, X. Chem. Sci. 2013, 4, 3712.
14. For selected reviews on C-H functionalization in organic synthesis, see: Godula, K.; Sames, D. Science 2006, 312, 67.
15. Brckl, T.; Baxter, R. D.; Ishihara, Y.; Baran, P. S. Acc. Chem. Res. 2012, 45, 826.
16. McMurray, L.; OHara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885.
17. Zhang, Q.; Chen, K.; Rao, W.-H.; Zhang, Y.; Chen, F.-J.; Shi, B.-F. Angew. Chem. Int. Ed. 2013, 52, 13588.
18. Sun, W.-W.; Cao, P.; Mei, R.-Q.; Li, Y.; Ma, Y.-L.; Wu, B. Org. Lett. 2014, 16, 480.
19. Wang, Z.; Ni, J.; Kuninobu, Y.; Kanai, M. Angew. Chem. Int. Ed. 2014, 53, 3496.
20. Wu, X.; Zhao, Y.; Zhang, G.; Ge, H. Angew. Chem. Int. Ed. 2014, 53, 3706.
21. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
22. Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965.
23. Tran, L. D.; Daugulis, O. Angew. Chem. Int. Ed. 2012, 51, 5188.
24. For a recent review and selected references, see: Rouquet, G.; Chatani, N. Angew. Chem. Int. Ed. 2013, 52, 11726.
25. Reddy, L. R.; Reddy, B. V. S.; Corey, E. J. Org. Lett. 2006, 8, 2819.
26. Feng, Y.; Wang, Y.; Landgraf, B.; Liu, S.; Chen, G. Org. Lett. 2010, 12, 3414.
27. Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984.
28. Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030.
29. Chen, K.; Hu, F.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 3906.
30. Pan, F.; Shen, P.-X.; Zhang, L.-S.; Wang, X.; Shi, Z.-J. Org. Lett. 2013, 15, 4758.
31. Li, M.; Dong, J.; Huang, X.; Li, K.; Wu, Q.; Song, F.; You, J. Chem. Commun. 2014, 50, 3944.
32. Aihara, Y.; Chatani, N. J. Am. Chem. Soc. 2014, 136, 898; and references therein.
33. Chen, F.-J.; Zhao, S.; Hu, F.; Chen, K.; Zhang, Q.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 4187.
34. Shaw, B. L. J. Am. Chem. Soc. 1975, 97, 3856.
35. Ting, C. P.; Maimone, T. J. Angew. Chem. Int. Ed. 2014, 53, 3115.