An improved procedure for the palladium-catalyzed oxidative carbonylation of β-amino alcohols to oxazolidin-2-ones

Journal of Organic Chemistry

Volumn 68, Issue 2, 2003, Pages 601-604

  Gabriele, Bartolo ^a   Mancuso, Raffaella ^a   Salerno, Giuseppe ^a   Costa, Mirco ^b  

^a UNIVERSITY OF CALABRIA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYLATION; CATALYSTS; PALLADIUM;

OXIDATIVE CYCLOCARBONYLATION;

ALCOHOLS;

2 AMINOPHENOL; AMINOALCOHOL; CARBON MONOXIDE; CARBONYL DERIVATIVE; OXAZOLIDIN 2 ONE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PALLADIUM; POTASSIUM IODIDE; UNCLASSIFIED DRUG;

ACID BASE BALANCE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBONYLATION; CATALYST; CHEMICAL REACTION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037462343     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026532a     Document Type: Article

References (49)

1. Gabriele, B.; Salerno, G.; Brindisi, D.; Costa, M.; Chiusoli, G. P. Org. Lett. 2000, 2, 625-627.
2. Pri-Bar, I.; Alper, H. Can. J. Chem. 1990, 68, 1544-1547.
3. Goldoni, G.; Marcheselli, L.; Pistoni, G.; Tassi, L.; Fanali, S. J. Chem. Soc., Faraday Trans. 1992, 88, 2003-2006.
4. Pearson, R. G.; Vogelsong, D. C. J. Am. Chem. Soc. 1958, 80, 1038-1043.
5. For some recent data on pharmacological activity of 5, see: Kim, D. S.; Jeong, H. J.; Bhat, K. P. L.; Park, S. Y.; Kang, S. H.; Yoo, E. H.; Lee, M.; Lee, H. W.; Krueger, R. J.; Kim, D. S. H. L. Planta Med. 2000, 66, 78-79. Igarashi, Y.; Keiichi, K.; Furumai, T., J. Antibiot. 1998, 51, 915-920.
6. For some recent data on pharmacological activity of 5, see: Kim, D. S.; Jeong, H. J.; Bhat, K. P. L.; Park, S. Y.; Kang, S. H.; Yoo, E. H.; Lee, M.; Lee, H. W.; Krueger, R. J.; Kim, D. S. H. L. Planta Med. 2000, 66, 78-79. Igarashi, Y.; Keiichi, K.; Furumai, T., J. Antibiot. 1998, 51, 915-920.
7. Formation of 5 from 3 and oxygen has been reported. For recent references, see: (a) Simandi, L. I.; Barna, T.; Nemeth, S. J. Chem. Soc., Dalton Trans. 1996, 473-478. (b) Maruyama, K.; Moriguchi, T.; Mashino, T.; Nishinaga, A. Chem. Lett. 1996, 819-820.
8. Formation of 5 from 3 and oxygen has been reported. For recent references, see: (a) Simandi, L. I.; Barna, T.; Nemeth, S. J. Chem. Soc., Dalton Trans. 1996, 473-478. (b) Maruyama, K.; Moriguchi, T.; Mashino, T.; Nishinaga, A. Chem. Lett. 1996, 819-820.
9. 4).
10. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
11. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
12. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
13. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
14. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
15. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
16. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
17. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
18. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
19. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
20. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
21. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
22. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
23. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
24. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
25. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
26. For a recent review on the importance of the development of new atom-economical processes, see: Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705. Gage, J. R.; Evans, D. A. Org. Synth. 1990, 68, 77-82. For a review on synthesis of 2, see Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. For some recent developments in oxazolidin-2-one synthesis, see: Feroci, M.; Gennaro, A.; Inesi, A.; Orsini, M.; Palombi, L. Tetrahedron Lett. 2002, 43, 5863-5865. Righi, G.; Potini, C.; Bovicelli, P. Tetrahedron Lett. 2002, 43, 5867-5869. Casado-Bellver, F. J.; Gonzalez -Rosende, M. E.; Asensio, A.; Jorda-Gregori, J. M.; Alvarez-Sorolla, A.; Sepulveda-Arques, J.; Orena, M.; Galeazzi, R. J. Chem. Soc., Perkin Trans. 1 2002, 1650-1654. Kawanami, H.; Ikushima, Y. Tetrahedron Lett. 2002, 43, 3841-3844. Coelho, F.; Rossi, R. C. Tetrahedron Lett. 2002, 43, 2797-2800. Tominaga, K.; Sasaki, Y. Synlett. 2002, 307-309. Lei, A. W.; Liu, G. S.; Lu, X. Y. J. Org. Chem. 2002, 67, 974-980. Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13. Enders, D.; Kallfass, U.; Nolte, B. Synlett. 2002, 33-36. Liu, G. S.; Lu, X. Y. Org. Lett. 2001, 3, 3879-3882. Bertau, M.; Burli, M.; Hungerbuhler, E.; Wagner, P. Tetrahedron: Asymm. 2001, 12, 2103-2107. Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Zappia, G. Org. Lett. 2001, 3, 2539-2541. Ariza, X.; Pineta, O.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 2001, 42, 4995-4999. Yu, C. Z.; Jiang,Y. Y.; Liu, B.; Hu, L. Q. Tetrahedron Lett. 2001, 42, 1449-1452.
27. Dialkyl carbonates were initially industrially prepared by the reaction between ROH and phosgene, the latter being in its turn obtained from the reaction between carbon monoxide and chlorine. In the past decades, methods based on oxidative carbonylation of alcohols have been developed (for recent reviews on the production and chemistry of dialkyl carbonates, see: Tundo, P.; Selva, M. Acc. Chem. Res. 2002, 35, 706-716; Delledonne, D.; Rivetti, F.; Romano, U. Appl. Catal. A: Gen. 2001, 221, 241-251). Clearly, the possibility to synthesize 2 starting directly from carbon monoxide rather than dialkyl carbonates represents an advantage from the standpoint of atom economy.8
28. Dialkyl carbonates were initially industrially prepared by the reaction between ROH and phosgene, the latter being in its turn obtained from the reaction between carbon monoxide and chlorine. In the past decades, methods based on oxidative carbonylation of alcohols have been developed (for recent reviews on the production and chemistry of dialkyl carbonates, see: Tundo, P.; Selva, M. Acc. Chem. Res. 2002, 35, 706-716; Delledonne, D.; Rivetti, F.; Romano, U. Appl. Catal. A: Gen. 2001, 221, 241-251). Clearly, the possibility to synthesize 2 starting directly from carbon monoxide rather than dialkyl carbonates represents an advantage from the standpoint of atom economy.8
29. Chiral oxazolidin-2-ones are widely used as chiral auxiliaries in many important asymmetric syntheses. For reviews, see: Evans, D. A. Aldrichim. Acta 1982, 15, 23-32. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichim. Acta 1997, 30, 3-12. For some recent examples, see: Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L.; Hu, Q.; Shi, W. J. Org. Chem. 2002, 67, 3802-3810. Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L. Helv. Chim. Acta 2001, 84, 3428-3432. Faita, G.; Paio, A.; Quadrelli, P. Rancati, F.; Senesi, P. Tetrahedron 2001, 57, 8313-8322.
30. Chiral oxazolidin-2-ones are widely used as chiral auxiliaries in many important asymmetric syntheses. For reviews, see: Evans, D. A. Aldrichim. Acta 1982, 15, 23-32. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichim. Acta 1997, 30, 3-12. For some recent examples, see: Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L.; Hu, Q.; Shi, W. J. Org. Chem. 2002, 67, 3802-3810. Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L. Helv. Chim. Acta 2001, 84, 3428-3432. Faita, G.; Paio, A.; Quadrelli, P. Rancati, F.; Senesi, P. Tetrahedron 2001, 57, 8313-8322.
31. Chiral oxazolidin-2-ones are widely used as chiral auxiliaries in many important asymmetric syntheses. For reviews, see: Evans, D. A. Aldrichim. Acta 1982, 15, 23-32. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichim. Acta 1997, 30, 3-12. For some recent examples, see: Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L.; Hu, Q.; Shi, W. J. Org. Chem. 2002, 67, 3802-3810. Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L. Helv. Chim. Acta 2001, 84, 3428-3432. Faita, G.; Paio, A.; Quadrelli, P. Rancati, F.; Senesi, P. Tetrahedron 2001, 57, 8313-8322.
32. Chiral oxazolidin-2-ones are widely used as chiral auxiliaries in many important asymmetric syntheses. For reviews, see: Evans, D. A. Aldrichim. Acta 1982, 15, 23-32. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichim. Acta 1997, 30, 3-12. For some recent examples, see: Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L.; Hu, Q.; Shi, W. J. Org. Chem. 2002, 67, 3802-3810. Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L. Helv. Chim. Acta 2001, 84, 3428-3432. Faita, G.; Paio, A.; Quadrelli, P. Rancati, F.; Senesi, P. Tetrahedron 2001, 57, 8313-8322.
33. Chiral oxazolidin-2-ones are widely used as chiral auxiliaries in many important asymmetric syntheses. For reviews, see: Evans, D. A. Aldrichim. Acta 1982, 15, 23-32. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichim. Acta 1997, 30, 3-12. For some recent examples, see: Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L.; Hu, Q.; Shi, W. J. Org. Chem. 2002, 67, 3802-3810. Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L. Helv. Chim. Acta 2001, 84, 3428-3432. Faita, G.; Paio, A.; Quadrelli, P. Rancati, F.; Senesi, P. Tetrahedron 2001, 57, 8313-8322.
34. Chiral oxazolidin-2-ones are widely used as chiral auxiliaries in many important asymmetric syntheses. For reviews, see: Evans, D. A. Aldrichim. Acta 1982, 15, 23-32. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. Ager, D. J.; Prakash, I.; Schaad, D. R. Aldrichim. Acta 1997, 30, 3-12. For some recent examples, see: Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L.; Hu, Q.; Shi, W. J. Org. Chem. 2002, 67, 3802-3810. Wu, Y. K.; Shen, X.; Tang, C. J.; Chen, Z. L. Helv. Chim. Acta 2001, 84, 3428-3432. Faita, G.; Paio, A.; Quadrelli, P. Rancati, F.; Senesi, P. Tetrahedron 2001, 57, 8313-8322.
35. Some molecules containing the oxazolidin-2-one moiety have shown interesting pharmaceutical activity. For recent leading references, see: Ahmed, S.; Adat, S.; Murrells, A.; Owen, C. P. Biochem. Biophys. Res. Commun. 2002, 294, 380-383. Mai, A.; Artico, M.; Esposito, M.; Sbardella, G.; Massa, S.; Befani, O.; Turini, P.; Giovannini, V.; Mondovi, B. J. Med. Chem. 2002, 45, 1180-1183; Seki, M.; Mori, K. Eur. J. Org. Chem. 1999, 2965-2967.
36. Some molecules containing the oxazolidin-2-one moiety have shown interesting pharmaceutical activity. For recent leading references, see: Ahmed, S.; Adat, S.; Murrells, A.; Owen, C. P. Biochem. Biophys. Res. Commun. 2002, 294, 380-383. Mai, A.; Artico, M.; Esposito, M.; Sbardella, G.; Massa, S.; Befani, O.; Turini, P.; Giovannini, V.; Mondovi, B. J. Med. Chem. 2002, 45, 1180-1183; Seki, M.; Mori, K. Eur. J. Org. Chem. 1999, 2965-2967.
37. Some molecules containing the oxazolidin-2-one moiety have shown interesting pharmaceutical activity. For recent leading references, see: Ahmed, S.; Adat, S.; Murrells, A.; Owen, C. P. Biochem. Biophys. Res. Commun. 2002, 294, 380-383. Mai, A.; Artico, M.; Esposito, M.; Sbardella, G.; Massa, S.; Befani, O.; Turini, P.; Giovannini, V.; Mondovi, B. J. Med. Chem. 2002, 45, 1180-1183; Seki, M.; Mori, K. Eur. J. Org. Chem. 1999, 2965-2967.
38. Recently, oxazolidin-2-ones have also found application as synthetic intermediates. For some leading references, see: Knight, J. G.; Tchabanenko, K. Tetrahedron 2002, 58, 6659-6664. Shen, Y. H.; Friestad, G. K. J. Org. Chem. 2002, 6236-6239. Marcantoni, E.; Mecozzi, T.; Petrini, M. J. Org. Chem. 2002, 67, 2989-2994. Gaul, C.; Seebach, D.; Helv. Chim. Acta 2002, 85, 772-787. Feroci, M.; Inesi, A.; Palombi, L.; Rossi, L. Tetrahedron: Asymm. 2001, 12, 2331. Morita, T.; Nagasawa, Y.; Yashiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897-899. Ishibashi, H.; Uegaki, M.; Sakai, M.; Takeda, Y. Tetrahedron 2001, 57, 2115-2120.
39. Recently, oxazolidin-2-ones have also found application as synthetic intermediates. For some leading references, see: Knight, J. G.; Tchabanenko, K. Tetrahedron 2002, 58, 6659-6664. Shen, Y. H.; Friestad, G. K. J. Org. Chem. 2002, 6236-6239. Marcantoni, E.; Mecozzi, T.; Petrini, M. J. Org. Chem. 2002, 67, 2989-2994. Gaul, C.; Seebach, D.; Helv. Chim. Acta 2002, 85, 772-787. Feroci, M.; Inesi, A.; Palombi, L.; Rossi, L. Tetrahedron: Asymm. 2001, 12, 2331. Morita, T.; Nagasawa, Y.; Yashiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897-899. Ishibashi, H.; Uegaki, M.; Sakai, M.; Takeda, Y. Tetrahedron 2001, 57, 2115-2120.
40. Recently, oxazolidin-2-ones have also found application as synthetic intermediates. For some leading references, see: Knight, J. G.; Tchabanenko, K. Tetrahedron 2002, 58, 6659-6664. Shen, Y. H.; Friestad, G. K. J. Org. Chem. 2002, 6236-6239. Marcantoni, E.; Mecozzi, T.; Petrini, M. J. Org. Chem. 2002, 67, 2989-2994. Gaul, C.; Seebach, D.; Helv. Chim. Acta 2002, 85, 772-787. Feroci, M.; Inesi, A.; Palombi, L.; Rossi, L. Tetrahedron: Asymm. 2001, 12, 2331. Morita, T.; Nagasawa, Y.; Yashiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897-899. Ishibashi, H.; Uegaki, M.; Sakai, M.; Takeda, Y. Tetrahedron 2001, 57, 2115-2120.
41. Recently, oxazolidin-2-ones have also found application as synthetic intermediates. For some leading references, see: Knight, J. G.; Tchabanenko, K. Tetrahedron 2002, 58, 6659-6664. Shen, Y. H.; Friestad, G. K. J. Org. Chem. 2002, 6236-6239. Marcantoni, E.; Mecozzi, T.; Petrini, M. J. Org. Chem. 2002, 67, 2989-2994. Gaul, C.; Seebach, D.; Helv. Chim. Acta 2002, 85, 772-787. Feroci, M.; Inesi, A.; Palombi, L.; Rossi, L. Tetrahedron: Asymm. 2001, 12, 2331. Morita, T.; Nagasawa, Y.; Yashiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897-899. Ishibashi, H.; Uegaki, M.; Sakai, M.; Takeda, Y. Tetrahedron 2001, 57, 2115-2120.
42. Recently, oxazolidin-2-ones have also found application as synthetic intermediates. For some leading references, see: Knight, J. G.; Tchabanenko, K. Tetrahedron 2002, 58, 6659-6664. Shen, Y. H.; Friestad, G. K. J. Org. Chem. 2002, 6236-6239. Marcantoni, E.; Mecozzi, T.; Petrini, M. J. Org. Chem. 2002, 67, 2989-2994. Gaul, C.; Seebach, D.; Helv. Chim. Acta 2002, 85, 772-787. Feroci, M.; Inesi, A.; Palombi, L.; Rossi, L. Tetrahedron: Asymm. 2001, 12, 2331. Morita, T.; Nagasawa, Y.; Yashiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897-899. Ishibashi, H.; Uegaki, M.; Sakai, M.; Takeda, Y. Tetrahedron 2001, 57, 2115-2120.
43. Recently, oxazolidin-2-ones have also found application as synthetic intermediates. For some leading references, see: Knight, J. G.; Tchabanenko, K. Tetrahedron 2002, 58, 6659-6664. Shen, Y. H.; Friestad, G. K. J. Org. Chem. 2002, 6236-6239. Marcantoni, E.; Mecozzi, T.; Petrini, M. J. Org. Chem. 2002, 67, 2989-2994. Gaul, C.; Seebach, D.; Helv. Chim. Acta 2002, 85, 772-787. Feroci, M.; Inesi, A.; Palombi, L.; Rossi, L. Tetrahedron: Asymm. 2001, 12, 2331. Morita, T.; Nagasawa, Y.; Yashiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897-899. Ishibashi, H.; Uegaki, M.; Sakai, M.; Takeda, Y. Tetrahedron 2001, 57, 2115-2120.
44. Recently, oxazolidin-2-ones have also found application as synthetic intermediates. For some leading references, see: Knight, J. G.; Tchabanenko, K. Tetrahedron 2002, 58, 6659-6664. Shen, Y. H.; Friestad, G. K. J. Org. Chem. 2002, 6236-6239. Marcantoni, E.; Mecozzi, T.; Petrini, M. J. Org. Chem. 2002, 67, 2989-2994. Gaul, C.; Seebach, D.; Helv. Chim. Acta 2002, 85, 772-787. Feroci, M.; Inesi, A.; Palombi, L.; Rossi, L. Tetrahedron: Asymm. 2001, 12, 2331. Morita, T.; Nagasawa, Y.; Yashiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897-899. Ishibashi, H.; Uegaki, M.; Sakai, M.; Takeda, Y. Tetrahedron 2001, 57, 2115-2120.
45. Kubota, Y.; Kodaka, M.; Tomohiro, T.; Okuno, H. J. Chem. Soc., Perkin Trans. 1 1993, 5-6.
46. Palaty, Y.; Abbott, F. S. J. Med. Chem. 1995, 38, 3398-3406.
47. Moreno-Mañas, M.; Padros, I. J. Heterocycl. Chem. 1993, 30, 1235-1239.
48. Denmark, S. E.; Stavenger, R. A.; Faucher, A.-M.; Edwards, J. P. J. Org. Chem. 1997, 62, 3375-3389.
49. King, S. W.; Natarajan, R.; Bembi, R.; Fife, T. H. J. Am. Chem. Soc. 1992, 114, 10715-10721.