Synlett 2014; 25(14): 1941-1945
DOI: 10.1055/s-0033-1338645
synpacts
© Georg Thieme Verlag Stuttgart · New York

Recent Progress in the Synthesis of Functionalized β-Lactams through Transition-Metal-Catalyzed C(sp3)–H Amidation

Qi Zhang
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China, Fax: +86(571)87951895   eMail: bfshi@zju.edu.cn
,
Kai Chen
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China, Fax: +86(571)87951895   eMail: bfshi@zju.edu.cn
,
Bing-Feng Shi*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China, Fax: +86(571)87951895   eMail: bfshi@zju.edu.cn
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 22. März 2014

Accepted after Revision: 14. April 2014

Publikationsdatum:
28. Mai 2014 (online)


Dedicate to Professor Li-Xin Dai on the occasion of his 90th birthday

Abstract

Transition-metal-catalyzed C–H activation and C–N bond formation has become one of the most important methods to generate heterocycles. Herein, recent progress in the synthesis of functionalized β-lactams through Pd- and Cu-catalyzed intramolecular C(sp3)–H amidation is highlighted.

 
  • References and Notes

    • 1a Chemistry and Biology of β-Lactam Antibiotics. Morin RB, Gorman M. Academic Press; New York: 1982
    • 1b Kamath A, Ojima I. Tetrahedron 2012; 68: 10640
    • 1c Böttcher T, Sieber SA. Med. Chem. Commun. 2012; 3: 408

      For selected reviews, see:
    • 2a France S, Weatherwax A, Taggi AE, Lectka T. Acc. Chem. Res. 2004; 37: 592
    • 2b Palomo C, Aizpurua JM, Ganboa I, Oiarbide M. Curr. Med. Chem. 2004; 11: 1837
  • 4 Neumann JJ, Rakshit S, Dröge T, Glorius F. Angew. Chem. Int. Ed. 2009; 48: 6892
    • 5a He G, Zhao Y, Zhang S, Lu C, Chen G. J. Am. Chem. Soc. 2012; 134: 3
    • 5b Nadres ET, Daugulis O. J. Am. Chem. Soc. 2012; 134: 7
    • 5c He G, Zhang S.-Y, Nack WA, Li Q, Chen G. Angew. Chem. Int. Ed. 2013; 52: 11124
  • 6 Ye X, He Z, Ahmed T, Weise K, Akhmedov NG, Petersen JL, Shi X. Chem. Sci. 2013; 4: 3712

    • For selected reviews on C–H functionalization in organic synthesis, see:
    • 7a Godula K, Sames D. Science 2006; 312: 67
    • 7b Brückl T, Baxter RD, Ishihara Y, Baran PS. Acc. Chem. Res. 2012; 45: 826
    • 7c McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
  • 8 Zhang Q, Chen K, Rao W.-H, Zhang Y, Chen F.-J, Shi B.-F. Angew. Chem. Int. Ed. 2013; 52: 13588
  • 9 Sun W.-W, Cao P, Mei R.-Q, Li Y, Ma Y.-L, Wu B. Org. Lett. 2014; 16: 480
    • 10a Wang Z, Ni J, Kuninobu Y, Kanai M. Angew. Chem. Int. Ed. 2014; 53: 3496
    • 10b Wu X, Zhao Y, Zhang G, Ge H. Angew. Chem. Int. Ed. 2014; 53: 3706
    • 11a Zaitsev VG, Shabashov D, Daugulis O. J. Am. Chem. Soc. 2005; 127: 13154
    • 11b Shabashov D, Daugulis O. J. Am. Chem. Soc. 2010; 132: 3965
    • 11c Tran LD, Daugulis O. Angew. Chem. Int. Ed. 2012; 51: 5188

      For a recent review and selected references, see:
    • 12a Rouquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
    • 12b Reddy LR, Reddy BV. S, Corey EJ. Org. Lett. 2006; 8: 2819
    • 12c Feng Y, Wang Y, Landgraf B, Liu S, Chen G. Org. Lett. 2010; 12: 3414
    • 12d Ano Y, Tobisu M, Chatani N. J. Am. Chem. Soc. 2011; 133: 12984
    • 12e Shang R, Ilies L, Matsumoto A, Nakamura E. J. Am. Chem. Soc. 2013; 135: 6030
    • 12f Chen K, Hu F, Zhang S.-Q, Shi B.-F. Chem. Sci. 2013; 4: 3906
    • 12g Pan F, Shen P.-X, Zhang L.-S, Wang X, Shi Z.-J. Org. Lett. 2013; 15: 4758
    • 12h Li M, Dong J, Huang X, Li K, Wu Q, Song F, You J. Chem. Commun. 2014; 50: 3944
    • 12i Aihara Y, Chatani N. J. Am. Chem. Soc. 2014; 136: 898 ; and references therein
  • 13 Chen F.-J, Zhao S, Hu F, Chen K, Zhang Q, Zhang S.-Q, Shi B.-F. Chem. Sci. 2013; 4: 4187
  • 14 Shaw BL. J. Am. Chem. Soc. 1975; 97: 3856
  • 15 Ting CP, Maimone TJ. Angew. Chem. Int. Ed. 2014; 53: 3115