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Volumn , Issue 3, 2009, Pages 395-398

Carbonylation with CO2 and phosphorus electrophiles: A convenient method for the synthesis of 2-oxazolidinones from 1,2-amino alcohols

(4) Paz, Jairo a Pérez Balado, Carlos a Iglesias, Beatriz a Muñoz, Luis a

a UNIVERSITY OF VIGO (Spain)

Author keywords

1,2 amino alcohols; Carbonylation; Guanidines; Oxazolidinones

Indexed keywords

EID: 62249143592 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087531 Document Type: Article

Times cited : (22)

References (38)

1
- 1842527630
- Coates, R. M, Denmark, S. E, Eds, John Wiley and Sons: New York
- (a) Evans, D. A.; Kim, A. S. In Handbook of Reagents for Organic Synthesis: Reagents, Auxiliaries and Catalysts for C-C Bonds; Coates, R. M.; Denmark, S. E., Eds.; John Wiley and Sons: New York, 1999, 91-101.
- (1999) Handbook of Reagents for Organic Synthesis: Reagents, Auxiliaries and Catalysts for C-C Bonds , pp. 91-101
- Evans, D.A.¹ Kim, A.S.²

2
- 0003643894
- Wiley: New York
- (b) Seydenpenne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995.
- (1995) Chiral Auxiliaries and Ligands in Asymmetric Synthesis
- Seydenpenne, J.¹

3
- 0038468227
- (c) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
- (1996) Chem. Rev , vol.96 , pp. 835
- Ager, D.J.¹ Prakash, I.² Schaad, D.R.³

4
- 62249175986
- (a) Gregory, W. A.; Brittelli, D. R.; Wang, C. L. J.; Wuonola, M. A.; McRipley, R. J.; Eustice, D. C.; Eberly, V. S.; Bartholomew, P. T.; Slee, A. M.; Forbes, M. J. Med. Chem. 1989, 32, 167.
- (1989) J. Med. Chem , vol.32 , pp. 167
- Gregory, W.A.¹ Brittelli, D.R.² Wang, C.L.J.³ Wuonola, M.A.⁴ McRipley, R.J.⁵ Eustice, D.C.⁶ Eberly, V.S.⁷ Bartholomew, P.T.⁸ Slee, A.M.⁹ Forbes, M.¹⁰

5
- 0030027833
- (b) Brickner, S. J.; Hutchinson, D. K.; Barbachyn, M. R.; Manninen, P. R.; Ulanowicz, D. A.; Garmon, S. A.; Crega, K. C.; Hendges, S. K.; Toops, D. S.; Ford, C. W.; Zurenko, G. E. J. Med. Chem. 1996, 39, 673.
- (1996) J. Med. Chem , vol.39 , pp. 673
- Brickner, S.J.¹ Hutchinson, D.K.² Barbachyn, M.R.³ Manninen, P.R.⁴ Ulanowicz, D.A.⁵ Garmon, S.A.⁶ Crega, K.C.⁷ Hendges, S.K.⁸ Toops, D.S.⁹ Ford, C.W.¹⁰ Zurenko, G.E.¹¹

6
- 0026532148
- (c) Park, C.-H.; Brittelli, D. R.; Wang, C. L.-J.; Marsh, F. D.; Gregory, W. A.; Wuonola, M. A.; McRipley, R. J.; Eberly, V. S.; Slee, A. M.; Forbes, M. J. Med. Chem. 1992, 35, 1156.
- (1992) J. Med. Chem , vol.35 , pp. 1156
- Park, C.-H.¹ Brittelli, D.R.² Wang, C.L.-J.³ Marsh, F.D.⁴ Gregory, W.A.⁵ Wuonola, M.A.⁶ McRipley, R.J.⁷ Eberly, V.S.⁸ Slee, A.M.⁹ Forbes, M.¹⁰

7
- 0025181123
- Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G. J. Am. Chem. Soc. 1990, 112, 2998.
- (1990) J. Am. Chem. Soc , vol.112 , pp. 2998
- Jones, T.K.¹ Reamer, R.A.² Desmond, R.³ Mills, S.G.⁴

8
- 0031898408
- Wouters, J. Curr. Med. Chem. 1998, 5, 137.
- (1998) Curr. Med. Chem , vol.5 , pp. 137
- Wouters, J.¹

9
- 0025666826
- Sibi, M. P.; Renhowe, P. A. Tetrahedron Lett. 1990, 35, 7407.
- (1990) Tetrahedron Lett , vol.35 , pp. 7407
- Sibi, M.P.¹ Renhowe, P.A.²

10
- 0000184462
- (a) Pridgen, L. N.; Prol, J. Jr.; Alexander, B.; Gillyard, L. J. Org. Chem. 1989, 54, 3231.
- (1989) J. Org. Chem , vol.54 , pp. 3231
- Pridgen, L.N.¹ Prol Jr., J.² Alexander, B.³ Gillyard, L.⁴

11
- 0026773203
- (b) Tamura, O.; Hashimoto, M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.; Hayakawa, I.; Akiba, T.; Terashima, S. Tetrahedron Lett. 1992, 33, 3487.
- (1992) Tetrahedron Lett , vol.33 , pp. 3487
- Tamura, O.¹ Hashimoto, M.² Kobayashi, Y.³ Katoh, T.⁴ Nakatani, K.⁵ Kamada, M.⁶ Hayakawa, I.⁷ Akiba, T.⁸ Terashima, S.⁹

12
- 0342519288
- (a) Sicker, D. Synthesis 1989, 875.
- (1989) Synthesis , pp. 875
- Sicker, D.¹

13
- 0032505206
- (b) Gibson, C. L.; Gillon, K.; Cook, S. Tetrahedron Lett. 1998, 39, 6733.
- (1998) Tetrahedron Lett , vol.39 , pp. 6733
- Gibson, C.L.¹ Gillon, K.² Cook, S.³

14
- 0002302741
- Close, W. J. J. Am. Chem. Soc. 1951, 73, 95.
- (1951) J. Am. Chem. Soc , vol.73 , pp. 95
- Close, W.J.¹

15
- 0005195930
- (a) Ishimaru, T. Nippon Kagaku Zasshi 1960, 81, 1589.
- (1960) Nippon Kagaku Zasshi , vol.81 , pp. 1589
- Ishimaru, T.¹

16
- 85016531617
- (b) Ishimaru, T. Nippon Kagaku Zasshi 1960, 81, 1428.
- (1960) Nippon Kagaku Zasshi , vol.81 , pp. 1428
- Ishimaru, T.¹

17
- 0035741914
- Fu, Y.; Baba, T.; Ono, Y. J. Catal. 2001, 197, 91.
- (2001) J. Catal , vol.197 , pp. 91
- Fu, Y.¹ Baba, T.² Ono, Y.³

18
- 35548960399
- (a) Peng, L.; Yuan, X.; Wang, S.; Lu, S. Tetrahedron 2007, 63, 12419.
- (2007) Tetrahedron , vol.63 , pp. 12419
- Peng, L.¹ Yuan, X.² Wang, S.³ Lu, S.⁴

19
- 33846039971
- (b) Liu, J. M.; Peng, X. G.; Liu, J. H.; Zheng, S. Z.; Sun, W.; Xia, C. G. Tetrahedron Lett. 2007, 48, 929.
- (2007) Tetrahedron Lett , vol.48 , pp. 929
- Liu, J.M.¹ Peng, X.G.² Liu, J.H.³ Zheng, S.Z.⁴ Sun, W.⁵ Xia, C.G.⁶

20
- 0004994046
- (c) Wilson, T. J. Org. Chem. 1986, 51, 2977.
- (1986) J. Org. Chem , vol.51 , pp. 2977
- Wilson, T.¹

21
- 0001636403
- (d) Imada, Y.; Mitsui, Y.; Ike, K.; Washizuka, K.; Murahashi, S. Bull. Chem. Soc. Jpn. 1996, 69, 2079.
- (1996) Bull. Chem. Soc. Jpn , vol.69 , pp. 2079
- Imada, Y.¹ Mitsui, Y.² Ike, K.³ Washizuka, K.⁴ Murahashi, S.⁵

22
- 4744338224
- (e) Li, F.; Xia, C. J. Catal. 2004, 227, 542.
- (2004) J. Catal , vol.227 , pp. 542
- Li, F.¹ Xia, C.²

23
- 0035858762
- (f) Chiarotto, I.; Feroci, M. Tetrahedron Lett. 2001, 42, 3451.
- (2001) Tetrahedron Lett , vol.42 , pp. 3451
- Chiarotto, I.¹ Feroci, M.²

24
- 0042405114
- (g) Gabriele, B.; Brindisi, D.; Salerno, G.; Costa, M.; Chiusoli, G. P. Org. Lett. 2000, 2, 625.
- (2000) Org. Lett , vol.2 , pp. 625
- Gabriele, B.¹ Brindisi, D.² Salerno, G.³ Costa, M.⁴ Chiusoli, G.P.⁵

25
- 0037462343
- (h) Gabriele, B.; Mancuso, R.; Salerno, G.; Costa, M. J. Org. Chem. 2003, 68, 601.
- (2003) J. Org. Chem , vol.68 , pp. 601
- Gabriele, B.¹ Mancuso, R.² Salerno, G.³ Costa, M.⁴

26
- 3242723482
- (i) Miller, A. W.; Nguyen, S. T. Org. Lett. 2004, 6, 2301.
- (2004) Org. Lett , vol.6 , pp. 2301
- Miller, A.W.¹ Nguyen, S.T.²

27
- 34447498554
- (j) Zheng, S.; Li, F.; Liu, J.; Xia, C. Tetrahedron Lett. 2007, 48, 5883.
- (2007) Tetrahedron Lett , vol.48 , pp. 5883
- Zheng, S.¹ Li, F.² Liu, J.³ Xia, C.⁴

28
- 4444239165
- (a) Dinsmore, C. J.; Mercer, S. P. Org. Lett. 2004, 6, 2885.
- (2004) Org. Lett , vol.6 , pp. 2885
- Dinsmore, C.J.¹ Mercer, S.P.²

29
- 0037525419
- (b) Bhanage, B. M.; Fujita, S.; Ikushima, Y.; Arai, M. Green Chem. 2003, 5, 340.
- (2003) Green Chem , vol.5 , pp. 340
- Bhanage, B.M.¹ Fujita, S.² Ikushima, Y.³ Arai, M.⁴

30
- 0036171633
- (c) Tominaga, K.-I.; Sasaki, Y. Synlett 2002, 307.
- (2002) Synlett , pp. 307
- Tominaga, K.-I.¹ Sasaki, Y.²

31
- 0001219223
- McGhee, W.; Riley, D.; Christ, K.; Pan, Y.; Parnas, B. J. Org. Chem. 1995, 60, 2820.
- (1995) J. Org. Chem , vol.60 , pp. 2820
- McGhee, W.¹ Riley, D.² Christ, K.³ Pan, Y.⁴ Parnas, B.⁵

32
- 37049106576
- Barton, D. H.; Elliot, J. D.; Géro, S. D. J. Chem. Soc., Perkin Trans. 1 1982, 2085.
- (1982) J. Chem. Soc., Perkin Trans. 1 , pp. 2085
- Barton, D.H.¹ Elliot, J.D.² Géro, S.D.³

33
- 37049074010
- Boyle, P. H.; Convery, M. A.; Davis, A. P.; Hosken, G. D.; Murray, B. A. J. Chem. Soc., Chem. Commun. 1992, 239.
- (1992) J. Chem. Soc., Chem. Commun , pp. 239
- Boyle, P.H.¹ Convery, M.A.² Davis, A.P.³ Hosken, G.D.⁴ Murray, B.A.⁵

34
- 41649113581
- García-Egido, E.; Fernández-Suárez, M.; Muñoz, L. J. Org. Chem. 2008, 73, 2909.
- (2008) J. Org. Chem , vol.73 , pp. 2909
- García-Egido, E.¹ Fernández-Suárez, M.² Muñoz, L.³

35
- 62249165553
- Purchased from Aldrich chemical company
- Purchased from Aldrich chemical company.

36
- 62249143296
- Representative Procedure for the Synthesis of 2-Oxazolidinones 4a-j A solution of (1S,2R)-norephedrine (3a, 210 mg, 1.39 mmol) and tetramethylphenylguanidine (290 mg, 1.52 mmol, 110 mol, in anhyd MeCN (10 mL) was cooled to -40°C with a dry ice-acetone bath. Carbon dioxide was slowly bubbled through the solution for 5 min, and then diphenylphosphoryl azide (DPPA, 0.30 mL, 1.39 mmol, 100 mol, was added dropwise. Carbon dioxide bubbling was maintained for a further 15 min, and the reaction mixture was stirred overnight while it was slowly allowed to reach 20°C. The resulting solution was concentrated almost to dryness. The residue was dissolved in CHCl3 (30 mL) and washed with a 10% Na 2CO3 (previously saturated with NaCl) solution (1x, The aqueous layer was extracted with CHCl3. The combined organic layers were washed with 1 M HCl (previously saturated with NaCl) solution 1x, The aqueous layer was furth
- 3).

37
- 62249139995
- Unpublished results
- Unpublished results.

38
- 0001256026
- McGhee, W.; Riley, D. J. Org. Chem. 1995, 60, 6205.
- (1995) J. Org. Chem , vol.60 , pp. 6205
- McGhee, W.¹ Riley, D.²

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