Chiral oxazolidinones from α-hydroxy oxazolidines: A new access to 1,2- amino alcohols

Tetrahedron Asymmetry

Volumn 9, Issue 22, 1998, Pages 3955-3958

  Agami, Claude ^a   Amiot, Franck ^a   Couty, François ^a   Dechoux, Luc ^a   Kaminsky, Christophe ^a   Venier, Olivier ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; OXAZOLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032573439     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00414-5     Document Type: Article

References (19)

1. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
2. Scott, J. S. In Asymmetric Synthesis; Morrisson, J. D., Ed.; Academic Press: Orlando, 1984; Vol. 4, pp. 1-226.
3. Durand, J. O.; Genet, J. P. Bull. Soc. Chim. Fr. 1994, 131, 612-619.
4. Kobayashi, S.; Hayashi, T.; Kawasuji, T. Tetrahedron Lett. 1994, 35, 9573-9576.
5. Pettit, G. R.; Burkett, D. B.; Barkoczy J.; Breneman, G. L.; Pettit, W. E. Synthesis 1996, 719-725.
6. For another recently disclosed strategy based on radical additions, see: Morita, T.; Matsunaga, H.; Sugiyama, E.; Ishisuka, T.; Kunieda, T. Tetrahedron Lett. 1998, 39, 7131-7134.
7. Agami, C.; Couty, F.; Hamon, L.; Venier, O. J. Org. Chem. 1997, 62, 2106-2112.
8. Agami, C.; Couty, F.; Lequesne, C. Tetrahedron 1995, 51, 4043-4056.
9. For some exemples, see: (a) Dhimane, H.; Vanucci, C.; Lhommet, G. Tetrahedron Lett. 1997, 38, 1415-1418. (b) Sadakane, M.; Vahle, R.; Schierle, K.; Kolter, D.; Steckhan, E. Synlett 1997, 95-96. (c) Danielmeier, K.; Schierle, K.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 2247-2248. (d) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocycles 1987, 26, 373-376. (e) Moolenar, M. J.; Speckamp, W. N.; Hiemstra, H.; Poetsch, E.; Casutt, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2391-2393.
10. For some exemples, see: (a) Dhimane, H.; Vanucci, C.; Lhommet, G. Tetrahedron Lett. 1997, 38, 1415-1418. (b) Sadakane, M.; Vahle, R.; Schierle, K.; Kolter, D.; Steckhan, E. Synlett 1997, 95-96. (c) Danielmeier, K.; Schierle, K.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 2247-2248. (d) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocycles 1987, 26, 373-376. (e) Moolenar, M. J.; Speckamp, W. N.; Hiemstra, H.; Poetsch, E.; Casutt, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2391-2393.
11. For some exemples, see: (a) Dhimane, H.; Vanucci, C.; Lhommet, G. Tetrahedron Lett. 1997, 38, 1415-1418. (b) Sadakane, M.; Vahle, R.; Schierle, K.; Kolter, D.; Steckhan, E. Synlett 1997, 95-96. (c) Danielmeier, K.; Schierle, K.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 2247-2248. (d) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocycles 1987, 26, 373-376. (e) Moolenar, M. J.; Speckamp, W. N.; Hiemstra, H.; Poetsch, E.; Casutt, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2391-2393.
12. For some exemples, see: (a) Dhimane, H.; Vanucci, C.; Lhommet, G. Tetrahedron Lett. 1997, 38, 1415-1418. (b) Sadakane, M.; Vahle, R.; Schierle, K.; Kolter, D.; Steckhan, E. Synlett 1997, 95-96. (c) Danielmeier, K.; Schierle, K.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 2247-2248. (d) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocycles 1987, 26, 373-376. (e) Moolenar, M. J.; Speckamp, W. N.; Hiemstra, H.; Poetsch, E.; Casutt, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2391-2393.
13. For some exemples, see: (a) Dhimane, H.; Vanucci, C.; Lhommet, G. Tetrahedron Lett. 1997, 38, 1415-1418. (b) Sadakane, M.; Vahle, R.; Schierle, K.; Kolter, D.; Steckhan, E. Synlett 1997, 95-96. (c) Danielmeier, K.; Schierle, K.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1996, 35, 2247-2248. (d) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocycles 1987, 26, 373-376. (e) Moolenar, M. J.; Speckamp, W. N.; Hiemstra, H.; Poetsch, E.; Casutt, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 2391-2393.
14. Agami, C.; Couty, F.; Venier, O. Synlett 1996, 511-512.
15. Agami, C.; Couty, F.; Lam, H.; Mathieu, H. Tetrahedron 1998, 54, 8783-8796.
16. See: Ishiguza, T.; Ishibushi, S.; Kunieda, T. Tetrahedron 1993, 49, 1841-1852 and Ref. 9b-d.
17. (a) Langlois, N.; Rojas, A. Tetrahedron 1993, 49, 77-82.
18. (b) Tung, R. D.; Rich, D. H. Tetrahedron Lett. 1987, 28, 1139-1142.
19. Meyers, A. I.; Burgess, L. E. J. Org. Chem. 1991, 56, 2294-2296, footnote 12.