Gold(I)-catalyzed formation of 5-methylene-1,3-oxazolidin-2-ones

Synlett

Volumn , Issue 17, 2006, Pages 2727-2730

  Buzas, Andrea ^a   Gagosz, Fabien ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

Gold catalysis; Oxazolidinones; Ring closure

Indexed keywords

5 METHYLENE 1,3 OXAZOLIDIN 2 ONE; CARBAMIC ACID DERIVATIVE; GOLD; OXAZOLIDINONE DERIVATIVE; TERT BUTYLCARBAMATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33750533954     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950253     Document Type: Article

References (37)

1. For the use of oxazolidinoe as asymmetric auxiliaries, see: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
2. (b) Evans, D. A. Aldrichimica Acta 1982, 15, 23.
3. For the use of oxazolidinone as a source of protected 1,2-amino alcohols, see: (a) Bhaket J.; Morris, K.; Stauffer, C. S.; Datta, A. Org. Lett. 2005, 7, 5875.
4. (b) Ayad, T.; Faugeroux, V.; Genisson, Y.; Andre, C.; Baltas, M.; Gorrichon, L. J. Org. Chem. 2004, 69, 8775.
5. For biologically active molecules possessing an oxazolidine fragment, see: (a) Puder, C.; Loya, S.; Hizi, A.; Zeeck, A. J. Nat. Prod. 2001, 64, 42.
6. (b) Thirkettle, J.; Alvarez, E.; Boyd, H.; Brown, M.; Diez, E.; Hueso, J.; Elson, S.; Fuslton, M.; Gershater, C.; Morata, M. L.; Perez, P. J. Antibiot. 2000, 53, 664.
7. For natural compounds possessing an oxazolidine fragment, see: (a) Pluotno, A.; Carmeli, S. Tetrahedron 2005, 61, 575.
8. (b) Hsieh, T.-J.; Chang, F.-R.; Chia, Y.-C.; Chen, C.-Y.; Lin, H.-C.; Chiu, H.-F.; Wu, Y.-C. J. Nat. Prod. 2001, 64, 1157.
9. Selected examples of oxazolidinones synthesis: (a) From amino alcohols, see for instance: Tarnowski, A.; Retz, O.; Baer, T.; Schmidt, R. Eur. J. Org. Chem. 2005, 1129.
10. (b) From aziridines, see for instance: Miller, A. W.; Nguten, S. T. Org. Lett. 2004, 6, 2301.
11. (c) From epoxides, see for instance: Mertin, R.; Murruzzu, C.; Pericas, M. A.; Riera, A. J. Org. Chem. 2005, 70, 2325.
12. From carbamates, see for instance: Tiecco, M.; Testaferri, L.; Temperini, A.; Terlizzi, R.; Bagnoli, L.; Marini, F.; Santi, C. Synthesis 2005, 579.
13. (e) From isocyanates, see for instance: Fuentes, A.; Martinez-Palou, R.; Jimenez-Vasquez, H. A.; Delgado, F.; Reyes, A.; Tamariz, J. Monatsh. Chem. 2005, 136, 177.
14. (a) Buzas, A.; Gagosz, F. Org. Lett. 2006, 8, 515.
15. (b) For a related transformation using homopropargylic alcohol derivatives, see: Kang, J.-E.; Shin, S. Synlett 2006, 717.
16. 2 catalysts, see: (c) Mezailles, N.; Ricard, L.; Gagosz, F. Org. Lett. 2005, 7, 4133.
17. (d) Buzas, A.; Istrate, F.; Gagosz, F. Org. Lett. 2006, 8, 1957.
18. For recent reviews on gold catalysis, see: (a) Hashmi, A. S. K. Angew. Chem. Int. Ed. 2005, 44, 6990.
19. (b) Hoffman-Röder, A.; Krause, N. Org. Biomol. Chem. 2005, 3, 387.
20. (c) Echavarren, A. M.; Nevado, C. Chem. Soc. Rev. 2004, 33, 431.
21. (d) Arcadi, A.; Di Giuseppe, S. Curr. Org. Chem. 2004, 8, 795.
22. (e) Hashmi, A. S. K. Gold Bull. 2003, 36, 3.
23. For some recent examples of alkyne activation by Au(I) complexes, see: (f) Sherry, B. D.; Maus, L.; Laforteza, B. N.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 8132.
24. (g) Marion, N.; Diez-Gonzales, S.; de Frémont, P.; Noble, A. R.; Nolan, S. P. Angew. Chem. Int. Ed. 2006, 45, 1.
25. (h) Zhang, L.; Wang, S. J. Am. Chem. Soc. 2006, 128, 1442.
26. (i) Genin, E.; Toullec, P.; Antoniotti, S.; Brancour, C.; Genêt, J. P.; Michelet, V. J. Am. Chem. Soc. 2006, 128, 3112.
27. (j) Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802.
28. (k) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962.
29. (l) Nieto-Oberhuber, C.; Lopez, S.; Echavarren, A. M. J. Am. Chem. Soc. 2005, 127, 6178.
30. (m) Nieto-Oberhuber, C.; Lopez, S.; Munoz, M. P.; Cardenas, D. J.; Bunel, E.; Nevado, C.; Echavarren, A. M. Angew. Chem. Int. Ed. 2005, 44, 6146.
31. (n) Markham, J. P.; Staben, S. P.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 9708.
32. (o) Antoniotti, S.; Genin, E.; Michelet, V.; Genêt, J. P. J. Am. Chem. Soc. 2005, 127, 9976.
33. Robles-Machin, R.; Adrio, J.; Carretero, J. C. J. Org. Chem. 2006, 71, 5023.
34. The work recently reported by Carretero and coworkers (see ref. 8) was only dealing with the synthesis of oxazolidinones substituted at the nitrogen and alkyne terminus.
35. 2.
36. 2N: 217.1103; found: 217.1103.
37. These substrates substituted at the propargylic position (5i-n) were synthesized according to the method developed by Petrini and coworkers. See, for instance: Mecozzi, T.; Petrini, M. J. Org. Chem. 1999, 64, 8970.