Synthesis of fused-β-lactams through selective gold-catalyzed oxycyclization of dioxolane-tethered enynes

Journal of Organic Chemistry

Volumn 78, Issue 18, 2013, Pages 8956-8965

  Alcaide, Benito ^a   Almendros, Pedro ^b   Martínez Del Campo, Teresa ^a   Torres, M Rosario ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ENYNOLS; HETEROCYCLIZATIONS; METAL-CATALYZED; PENDANT GROUPS; TETRA-HYDROFURAN;

AMIDES; CATALYSIS; GOLD;

CYCLIZATION;

BETA LACTAM DERIVATIVE; GOLD; OXYTETRACYCLINE; TETRAHYDROFURAN;

ARTICLE; CYCLIZATION; HETEROCYCLIZATION; SYNTHESIS;

EID: 84884581487     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401390k     Document Type: Article

References (47)

1. Payne, D. J. Science 2008, 321, 1644
2. Spencer, J.; Walsh, T. Angew. Chem., Int. Ed. 2006, 45, 1022
3. Fisher, J. F.; Meroueh, S. O.; Mobashery, S. Chem. Rev. 2005, 105, 395
4. Veinberg, G.; Vorona, M.; Shestakova, I.; Kanepe, I.; Lukevics, E. Curr. Med. Chem. 2003, 10, 1741
5. Miller, T. M.; Cleveland, D. W. Science 2005, 307, 361
6. Banik, B. K.; Banik, E.; Becker, F. F. In Topics in Heterocyclic Chemistry; Banik, B. K., Ed.; Springer-Verlag: Berlin, Heidelberg, 2010; Vol. 22, p 349.
7. Kamath, A.; Ojima, I. Tetrahedron 2012, 68, 10640
8. Alcaide, B.; Almendros, P. Chem. Rec. 2011, 11, 311
9. Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437
10. Modern Gold Catalyzed Synthesis; Hashmi, A. S. K.; Toste, F. D., Eds.; Wiley-VCH: Weinheim, 2012.
11. Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448
12. Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657
13. Alcaide, B.; Almendros, P.; Alonso, J. M. Org. Biomol. Chem. 2011, 9, 4405
14. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2010, 49, 5232
15. Science of Synthesis; Thomas, E. J., Ed.; Thieme: Stuttgart, 2008; Vol. 43.
16. Acetylene Chemistry; Diederich, F.; Stang, P. J.; Tykwinski, R. R., Eds.; Wiley-VCH: New York, 2005. For reviews on the construction of heterocycles by alkyne π-activation, see
17. Rudolph, M.; Hashmi, A. S. K. Chem. Commun. 2011, 47, 6536
18. Das, A.; Sohel, S. M. A.; Liu, R.-S. Org. Biomol. Chem. 2010, 8, 960
19. Yamamoto, Y.; Gridnev, I. D.; Patil, N. T.; Jin, T. Chem. Commun. 2009, 5075
20. Kirsch, S. F. Synthesis 2008, 3183
21. McDonald, F. E. Chem.-Eur. J. 1999, 5, 3103
22. Yu, X.; Zhang, J. Chem.-Eur. J. 2012, 18, 12945
23. Bender, G.; Wiegand, T.; Eckert, H.; Fröhlich, R.; Daniliuc, C. G.; Mück-Lichtenfeld, C.; Ndambuki, S.; Ziegler, T.; Kehr, G.; Erker, G. Angew. Chem., Int. Ed. 2012, 51, 8846
24. Dateer, R. B.; Pati, K.; Liu, R.-S. Chem. Commun. 2012, 48, 7200
25. Gai, B. M.; Stein, A. L.; Roehrs, J. A.; Bilheri, F. N.; Nogueira, C. W.; Zeni, G. Org. Biomol. Chem. 2012, 10, 798
26. Zhong, M.-J.; Wang, X.-C.; Zhu, H.-T.; Hu, J.; Liu, L.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2012, 77, 10955
27. Han, Z.-Y.; Chen, D.-F.; Wang, Y.-Y.; Guo, R.; Wang, P.-S.; Wang, C. J. Am. Chem. Soc. 2012, 134, 6532
28. Hashmi, A. S. K.; Ghanbari, M.; Rudolph, M.; Rominger, F. Chem.-Eur. J. 2012, 18, 8113
29. Kotikalapudi, R.; Swamy, K. C. K. Tetrahedron Lett. 2012, 53, 3831
30. Du, X.; Song, F.; Lu, Y.; Chen, H.; Liu, Y. Tetrahedron 2009, 65, 1839
31. Mollet, K.; D'hooghe, M.; De Kimpe, N. Tetrahedron 2012, 68, 10787
32. Zhang, Z.; Zhang, Q.; Ni, Z.; Liu, Q. Chem. Commun. 2010, 1269
33. Alcaide, B.; Almendros, P.; Martínez del Campo, T.; Carrascosa, R. Eur. J. Org. Chem. 2010, 4912
34. Leemans, E.; D'hooghe, M.; Dejaegher, Y.; Törnroos, K. W.; De Kimpe, N. Eur. J. Org. Chem. 2010, 352
35. Alcaide, B.; Almendros, P.; Martínez del Campo, T.; Soriano, E.; Marco-Contelles, J. L. Chem.-Eur. J. 2009, 15, 1901
36. Alcaide, B.; Almendros, P.; Aragoncillo, C. Org. Lett. 2000, 2, 1411
37. Alcaide, B.; Almendros, P.; Martínez del Campo, T. Org. Biomol. Chem. 2012, 10, 7603
38. Bew, S. P.; Hiatt-Gipson, G. D.; Lovell, J. A.; Poullain, C. Org. Lett. 2012, 14, 456
39. Yabe, Y.; Sawama, Y.; Monguchi, Y.; Sajiki, H. Chem.-Eur. J. 2013, 19, 484
40. It is very interesting and strange that the observed epimerization occurs at the α position of CO in the presence of Pt but not in the presence of Ag, when it is well known that AgOTf is able to speed up tautomeric equilibria; e.g., see: Dell'Acqua, M.; Abbiati, G.; Arcadi, A.; Rossi, E. Org. Biomol. Chem. 2011, 9, 7836 We thank a reviewer for calling this to our attention.
41. Shao, X.; Carpenter, G. M.; Desmond, T. J.; Sherman, P.; Quesada, C. A.; Fawaz, M.; Brooks, A. F.; Kilbourn, M. R.; Albin, R. L.; Frey, K. A.; Scott, P. J. H. ACS Med. Chem. Lett. 2012, 3, 936
42. Cai, L.; Lu, S.; Pike, V. W. Eur. J. Org. Chem. 2008, 2853
43. Allard, M.; Fouquet, E.; James, D.; Szlosek-Pinaud, M. Curr. Med. Chem. 2008, 15, 235
44. Atzrodt, J.; Derdau, V.; Fey, T.; Zimmermann, J. Angew. Chem., Int. Ed. 2007, 46, 7744
45. Duschek, A.; Kirsch, S. F. Angew. Chem., Int. Ed. 2008, 47, 5703
46. Gaillard, S.; Bosson, J.; Ramón, R. S.; Nun, P.; Slawin, A. M. Z.; Nolan, S. P. Chem.-Eur. J. 2010, 16, 13729
47. However, despite proving that the silver activators themselves are unreactive, there are examples of gold(I)-catalyzed reactions where Ag(I) salts affected either activity or selectivity: Wang, D.; Cai, R.; Sharma, S.; Jirak, J.; Thummanapelli, S. K.; Akhmedov, N. G.; Zhang, H.; Liu, X.; Petersen, J. L.; Shi, X. J. Am. Chem. Soc. 2012, 134, 9012