Desymmetric ring-opening of meso-epoxides with anilines: A simple way to chiral β-amino alcohols

Tetrahedron Asymmetry

Volumn 9, Issue 10, 1998, Pages 1747-1752

  Hou, Xue Long ^a   Wu, Jie ^a   Dai, Li Xin ^a   Xia, Li Jun ^a   Tang, Ming Hua ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; ANILINE DERIVATIVE; EPOXIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; OPTICAL ROTATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032557714     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00153-0     Document Type: Article

References (31)

1. Forth, W.; Henschler, D.; Rummel, W., eds, Pharmakologie und Toxikologie, Wissenschaftsverlag: Mannheim, 1988.
2. Whelton, A.; Neu, H. C., eds, The Aminoglycosides, Marcel Dekker: New York, 1982.
3. Horii, S.; Fukase, H.; Matsuo, T.; Kameda, Y.; Asano, N.; Matsui, K. J. Med. Chem. 1986, 29, 1038.
4. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
5. Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
6. (a) Yamashita, H. Bull. Chem. Soc. Jpn 1988, 61, 1213;
7. (b) Yamashita, H. Chem. Lett. 1987, 525;
8. (c) Emziane, M.; Sutowardoyo, K. I.; Sinou, D. J. Organomet. Chem. 1988, 346, C7;
9. (d) Hayashi, M.; Kohmura, K.; Oguni, N. Synlett 1991, 774;
10. (e) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768;
11. (f) Adolfsson, H.; Moberg, C. Tetrahedron: Asymmetry 1995, 6, 2023;
12. (g) Fu, X. L.; Wu, S. H. Synth. Commun. 1997, 27, 1677.
13. Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans 1 1994, 2597.
14. Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433.
15. Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623.
16. (a) Li, A. H.; Dai, L. X.; Hou, X. L.; Huang, Y. Z.; Li, F. W. J. Org. Chem. 1996, 61, 489;
17. (b) Li, A. H.; Dai, L. X.; Hou, X. L.; Chen, M. B. J. Org. Chem. 1996, 61, 4641;
18. (c) Zhou, Y. G.; Li, A. H.; Hou, X. L.; Dai, L. X. Chem. Commun. 1996, 1353;
19. (d) Li, A. H.; Zhou, Y. G.; Dai, L. X.; Hou, X. L.; Xia, L. J.; Lin, L. Angew. Chem. Int. Ed. Engl. 1997, 36, 1317;
20. (e) Hou, X. L.; Yang, X. F.; Dai, L. X.; Chen, X. F. Chem. Commun. 1998, 747.
21. (a) Kissel, C. L.; Richborn, B. J. Org. Chem. 1972, 37, 2060;
22. (b) Overmann, L. E.; Flippin, L. A. Tetrahedron Lett. 1981, 22, 195;
23. (c) Fiorenza, M.; Ricci, A.; Taddei, M.; Tassi, D. Synthesis 1983, 640;
24. (d) Papini, M.; Ricci, A.; Taddei, M.; Seconi, G.; Dembech, P. J. Chem. Soc., Perkin Trans 1 1984, 2261;
25. (e) Carre, M. C.; Houmouou, J. P.; Caubere, P. Tetrahedron Lett. 1985, 26, 3107;
26. (f) Atkins, R. K.; Frazier, J.; Moore, L. L.; Weigel, L. O. Tetrahedron Lett. 1986, 27, 2451;
27. (g) Fujiwara, M.; Imada, M.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1989, 30, 739;
28. (h) Yamada, J.; Yumoto, M.; Yamamoto, Y. Tetrahedron Lett. 1989, 30, 4255.
29. Katritzky, A. R.; Akutagawa, K.; Fan, W. Acta Chim. Sin. 1989, 471.
30. Alcaide, B.; Arjona, O.; Fernandez, P. R.; Plumet, J.; Rodriguez, I.; Santesmases, M. J. J. Chem. Res., Synop. 1988, 98.
31. Eisch, J. J.; Dua, S. K.; Kovacs, C. A. J. Org. Chem. 1987, 52, 4437.