A novel one-pot synthesis of oxazolidinones through direct introduction of CO2 into allylamine derivatives

Tetrahedron Letters

Volumn 55, Issue 7, 2014, Pages 1379-1383

  Soldi, Laura ^a   Massera, Chiara ^a   Costa, Mirco ^a   Della Ca', Nicola ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

Allylamine; Carbon dioxide fixation; One pot synthesis; Oxazolidinone; Supercritical fluids

Indexed keywords

ALLYLAMINE DERIVATIVE; CARBON DIOXIDE; OXAZOLIDINONE DERIVATIVE; 2 OXAZOLIDINONE DERIVATIVE;

ARTICLE; CARBOXYLATION; CHEMICAL REACTION; COVALENT BOND; CYCLIZATION; ELECTRON; ONE POT SYNTHESIS; CATALYST; DIASTEREOISOMER; DISSOCIATION; ELECTROPHILICITY; HIGH TEMPERATURE; NUCLEOPHILICITY; REACTION TIME; X RAY DIFFRACTION;

EID: 84893727457     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.01.029     Document Type: Article

References (48)

1. M. Aresta Carbon Dioxide as Chemical Feedstock 2010 Wiley-VCH Weinheim
2. M. Aresta, and A. Dibenedetto Dalton Trans. 2007 2975 2992
3. D.J. Darensbourg Chem. Rev. 107 2007 2388 2410
4. L. Ackermann Angew. Chem., Int. Ed. 50 2011 3842 3844
5. Y. Zhang, and S.N. Riduan Angew. Chem., Int. Ed. 50 2011 6210 6212
6. A.-H. Liu, Y.-N. Li, and L.-N. He Pure Appl. Chem. 84 2012 581 602
7. D.A. Evans, J. Bartroli, and T.L. Shih J. Am. Chem. Soc. 103 1981 2127 2129
8. B. Gabriele, R. Mancuso, G. Salerno, and M. Costa J. Org. Chem. 68 2003 601 604
9. B. Gabriele, G. Salerno, D. Brindisi, M. Costa, and G.P. Chiusoli Org. Lett. 2 2000 625 627
10. (a) Lynn, J. W. U.S. Patent 2,975,187, 1961
11. (b) Steele, A. B. U.S. Patent 2,868,801, 1959.
12. Q.-W. Song, Y.-N. Zhao, L.-N. He, J. Gao, and Z.-Z. Yang Curr. Catal. 1 2012 107 124
13. Y. Wu, and G. Liu Tetrahedron Lett. 52 2011 6450 6452
14. C. Phung, R.M. Ulrich, M. Ibrahim, N.T.G. Tighe, D.L. Lieberman, and A.R. Pinhas Green Chem. 13 2011 3224 3229
15. H.-F. Jiang, J.-W. Ye, C.-R. Qi, and L.-B. Huang Tetrahedron Lett. 51 2010 928 932
16. H. Kawanami, H. Matsumoto, and Y. Ikushima Chem. Lett. 34 2005 60 61
17. H. Kawanami, and Y. Ikushima Tetrahedron Lett. 43 2002 3841 3844
18. J. Zhao, and H. Jiang Tetrahedron Lett. 53 2012 6999 7002
19. T. Mitsudo, Y. Hori, Y. Yamakawa, and Y. Watanabe Tetrahedron Lett. 28 1987 4417 4418
20. (b) Dimroth, P.; Pasedach, H. (BASF) Ger. Patent (DAS) 1,098,953, 1961; Chem. Abstr. 1962, 56, 2453
21. (c) Dimroth, P.; Pasedach, H. Ger. Patent (DAS) 1,164,411, 1964; Chem. Abstr. 1964, 60, 14510
22. C. Bruneau, and P.H. Dixneuf J. Mol. Catal. 74 1992 97 107 and references therein
23. S. Yoshida, K. Fukui, S. Kikuchi, and T. Yamada Chem. Lett. 38 2009 786 787
24. M. Costa, G.P. Chiusoli, and M. Rizzardi Chem. Commun. 1996 1699 1700
25. M. Costa, G.P. Chiusoli, D. Taffurelli, and G. Dalmonego J. Chem. Soc., Perkin Trans. 1 1998 1541 1546
26. Y. Kayaki, M. Yamamoto, T. Suzuki, and T. Ikariya Green Chem. 8 2006 1019 1021
27. W.D. McGhee, and D.P. Riley Organometallics 11 1992 900 907
28. Y. Yoshida, and S. Inoue Chem. Lett. 6 1977 1375 1376
29. M. Yoshida, Y. Ohsawa, K. Sugimoto, H. Tokuyama, and M. Ihara Tetrahedron Lett. 48 2007 8678 8682
30. E. Garcia-Egido, I. Fernandez, and L. Munoz Synth. Commun. 36 2006 3029 3042
31. T. Toda, and Y. Kitagawa Angew. Chem. 99 1987 366 367 Angew. Chem., Int. Ed. Engl. 1987, 26, 334-335
32. Y. Takeda, S. Okumura, S. Tone, I. Sasaki, and S. Minakata Org. Lett. 14 2012 4874 4877
33. I. Fernandez, and L. Munoz Tetrahedron: Asymmetry 17 2006 2548 2557
34. D. Belli Dell'Amico, F. Calderazzo, L. Labella, F. Marchetti, and G. Pampaloni Chem. Rev. 103 2003 3857 3897
35. P.G. Jessop, T. Ikariya, and R. Noyori Chem. Rev. 99 1999 475 494
36. J.M. De Simone, and W. Tumas Green Chemistry Using Liquid and Supercritical Carbon Dioxide 2003 Oxford University Press New York
37. P.G. Jessop, and W. Leitner Chemical Synthesis Using Supercritical Fluids 1999 Wiley-VCH Weinheim
38. E.J. Beckmann J. Supercrit. Fluids 28 2004 121 191
39. M. Yoshida, N. Hara, and S. Okuyama Chem. Commun. 2000 151 152
40. M. Abla, J.-C. Choi, and T. Sakakura Chem. Commun. 2001 2238 2239
41. M. Selva, P. Tundo, and A. Perosa Tetrahedron Lett. 43 2002 1217 1219
42. O. Ihata, Y. Kayaki, and T. Ikariya Angew. Chem., Int. Ed. 43 2004 717 719
43. For the formation mechanism of carbamate derivatives see: M. Aresta, and E. Quaranta J. Org. Chem. 53 1988 4153 4154
44. M. Aresta, and E. Quaranta J. Chem. Soc., Dalton Trans. 1992 1893 1899
45. M. Aresta, and E. Quaranta Tetrahedron 48 1992 1515 1530
46. A. Inesi, V. Mucciante, and L. Rossi J. Org. Chem. 63 1998 1337 1338
47. A. Belforte, and F. Calderazzo J. Chem. Soc., Dalton Trans. 1989 1007 1009
48. A. Bongini, G. Cardillo, M. Orena, G. Porzi, and S. Sandri Tetrahedron 43 1987 4377 4383