Regio- and stereoselective opening of oxiranes through neighbouring group participation: Stereocontrolled synthesis of enantiopure hydroxylated oxazolidin-2-ones

European Journal of Organic Chemistry

Volumn , Issue 12, 1999, Pages 3483-3488

  Langlois, Nicole ^a   Moro, Alberto ^b  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^b UNIVERSITY OF GENOA   (Italy)

Author keywords

Aminodiols; Epoxide ring opening; Epoxides; Neighbouring group assistance; Oxazolidinones; Pyrrolidinones

Indexed keywords

2 PYRROLIDONE DERIVATIVE; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; OXAZOLIDINE DERIVATIVE;

ARTICLE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032757345     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199912)1999:12<3483::AID-EJOC3483>3.0.CO;2-E     Document Type: Article

References (42)

1. D. Griffart-Brunet, N. Langlois, Tetrahedron Lett. 1994, 35, 2889-2890 and references therein.
2. [2a] A. Hosaka, S. Ichikawa, H. Shindo, T. Sato, Bull. Chem. Soc. Jpn. 1989, 62, 797-799.
3. [2b] N. Ikota, Chem. Pharm. Bull. 1989, 37, 3399-3402.
4. Y. Ryu, G. Kim, J. Org. Chem. 1995, 60, 103-108.
5. Y. Huang, D. R. Dalton, P. J. Carroll, J. Org. Chem. 1997, 62, 372-376.
6. [5a] R. J. Nash, L. E. Fellows, J. V. Dring, G. W. J. Fleet, A. E. Derome, T. A. Hamor, A. M. Scofield, D. J. Watkin, Tetrahedron Lett. 1988, 29, 2487-2490.
7. [5b] G. W. J. Fleet, M. Haraldsson, R. J. Nash, L. E. Fellows, Tetrahedron Lett. 1988, 29, 5441-5444.
8. [5c] R. J. Nash, L. E. Fellows, A. C. Plant, G. W. J. Fleet, A. E. Derome, P. D. Baird, M. P. Hegarty, A. M. Scofield, Tetrahedron 1988, 44, 5959-5964.
9. [6a] N. Ikotai Heterocycles 1995, 41, 983-994.
10. [6b] Z.-C. Shi, G. Q. Lin, Tetrahedron: Asymm. 1995, 6, 2907-2910 and references therein.
11. [6c] H. Yoda, T. Nakajima, H. Yamazaki, K. Takabe, Heterocycles 1995, 41, 2423-2426.
12. [6d] U. Veith, O. Schwardt, V. Jäger, Synlett. 1996, 1181-1183.
13. [6d] P. Delair, E. Brot, A. Kanazawa, A. E. Greene, J. Org. Chem. 1999, 64, 1383-1386.
14. [7a] M. Hashimoto, M. Matsumoto, K. Yamada, S. Terashima, Tetrahedron Lett. 1994, 35, 2207-2210.
15. [7b] Y. Konda, T. Machida, M. Akaiwa, K. Takeda, Y. Harigaya, Heterocycles 1996, 43, 555-565.
16. [7c] R. S. Coleman, A. J. Carpenter, Tetrahedron 1997, 53, 16313-16326.
17. [7d] R. S. Coleman, Synlett. 1998, 1031-1039.
18. D. Griffart-Brunet, N. Langlois, Tetrahedron Lett. 1994, 35, 119-122.
19. C. Herdeis, H. P. Hubmann, H. Lotter, Tetrahedron: Asymmetry 1994, 5, 119-128.
20. S. K. Panday, N. Langlois, Synth. Comm. 1997, 27, 1373-1384.
21. C. Herdeis, A. Aschenbrenner, A. Kirfel, F. Schwabenländer, Tetrahedron: Asymm. 1997, 8, 2421-2432.
22. Preliminary communication: N. Langlois, A. Moro, XVIIIth European Colloquium on Heterocyclic Chemistry, Oct. 4th-7th, 1998, Rouen, France.
23. D. L. Flynn, R. E. Zelle, P. A. Grieco, J. Org. Chem. 1983, 48, 2424-2426.
24. K. Mori, M. Tominaga, T. Takigawa, M. Matsui, Synthesis 1973, 790-791.
25. [15a] S. Hünig, R. Schaller, Angew. Chem. Int. Ed. Engl. 1982, 21, 36-49.
26. [15b] R. G. Andrew, R. E. Conrow, J. D. Elliott, W. S. Johnson, S. Ramezani, Tetrahedron Lett. 1987, 28, 6535-6538.
27. [15c] A. Schoenfelder, A. Mann, Synth. Comm. 1990, 20, 2585-2588.
28. [15d] S. K. Panday, N. Langlois, Tetrahedron Lett. 1995, 36, 8205-8208.
29. N. Langlois, O. Calvez, M. O. Radom, Tetrahedron Lett. 1997, 38, 8037-8040.
30. This amine was selected to take advantage of the low pK of the hydroxamates in further studies: P. G. Mattingly, J. F. Kervin Jr, M. J. Miller, J. Am. Chem. Soc. 1979, 101, 3983-3985.
31. [18a] M. C. Di Giovanni, D. Misiti, G. Zappia, G. Delle Monache, Tetrahedron 1993, 49, 11321-11328.
32. [18b] G. Delle Monache, M. C. Di Giovanni, D. Misiti, G. Zappia, Tetrahedron: Asymmetry 1997, 8, 231-243.
33. K. A. Parker, R. O'Fee, J. Am. Chem. Soc. 1983, 105, 654-655.
34. Y. Guindon, A. Slassi, E. Ghiro, G. Bantle, G. Jung, Tetrahedron Lett. 1992, 33, 4257-4260.
35. C. Agami, F. Couty, O. Venier, Synlett. 1995, 1027-1028.
36. S. J. Kemp, J. Bao, S. F. Pedersen, J. Org. Chem. 1996, 61, 7162-7167.
37. [23a] S. Futagawa, T. Inui, T. Shiba, Bull. Chem. Soc. Jpn. 1973, 46, 3308-3310.
38. [23b] D. D. Dhavale, L. Gentilucci, M. G. Piazza, C. Trombini, Liebigs Ann. Chem. 1992, 1289-1295 and references therein.
39. [24a] C. Agami, F. Couty, L. Hamon, O. Venier, Tetrahedron Lett. 1993, 34, 4509-4512.
40. [24b] T. P. Curran, M. P. Pollastri, S. M. Abelleira, R. J. Messier, T. A. McCollum, C. G. Rowe, Tetrahedron Lett. 1994, 35, 5409-5412.
41. [24c] J. W. Lee, J. H. Lee, H. J. Son, Y. K. Choi, G. J. Yoon, M. H. Park, Synth. Comm. 1996, 26, 83-88.
42. N. Langlois, N. Van Bac, N. Dahuron, J. M. Delcroix, A. Deyine, D. Griffart-Brunet, A. Chiaroni, C. Riche, Tetrahedron 1995, 51, 3571-3586.