Modular synthesis of chiral homo- and heterotrisoxazolines. Improving the enantioselectivity in the asymmetric Michael addition of indole to benzylidene malonate

Journal of Organic Chemistry

Volumn 70, Issue 15, 2005, Pages 6108-6110

  Ye, Meng Chun ^a   Li, Bin ^a   Zhou, Jian ^a   Sun, Xiu Li ^a   Tang, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; SYNTHESIS (CHEMICAL);

CHIRALS; DEPROTONATION; MODULAR SYNTHESIS; TRISOXAZOLINES;

AROMATIC COMPOUNDS;

2 CHLOROMETHYLOXAZOLINE; BENZYLIDENE DERIVATIVE; BENZYLIDENE MALONATE; BISOXAZOLINE DERIVATIVE; HETEROTRISOXAZOLINE DERIVATIVE; INDOLE DERIVATIVE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; MICHAEL ADDITION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 22244469405     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050595m     Document Type: Article

References (39)

1. Reviews: (a) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
2. (b) Jørgensen, K. A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res. 1999, 32, 605.
3. (c) Pfaltz, A. J. Heterocycl. Chem. 1999, 36, 1437.
4. (d) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
5. (e) Meyers, A. I. J. Heterocycl. Chem. 1998, 35, 991.
6. (f) Reiser, O. Nachr. Chem. Technol. Lab. 1996, 44, 744.
7. (g) Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
8. (h) Pfaltz, A. Acc. Chem. Res. 1993, 26, 339.
9. (i) Bolm, C. Angew. Chem. 1991, 103, 556.
10. For chiral trisoxazolines, see: (a) Kim, S.-G.; Seong, H. R.; Kim, J.; Ahn, K. H. Tetrahedron Lett. 2004, 45, 6835.
11. (b) Rocchetti, M. T.; Fino, V.; Capriati, V.; Florio, S.; Luisi, R. J. Org. Chem. 2003, 68, 1394.
12. (c) Bellemin-Laponnaz, S.; Gade, L. H. Angew. Chem., Int. Ed. 2002, 41, 3473.
13. (d) Kim, S.-G.; Ahn, K. H. Tetrahedron Lett. 2001, 42, 4175.
14. (e) Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3941.
15. (f) Chuang, T.-H.; Fang, J.-M. Bolm, C. Synth. Commun. 2000, 30, 1627.
16. (g) Chan, T. H. Zheng, G. Z. Can. J. Chem. 1997, 75, 629.
17. (h) Kawasaki, K.; Katsuki, T. Tetrahedron 1997, 53, 6337.
18. (i) Kawasaki, K.; Tsumura, S.; Katsuki, T. Synlett 1995, 1245.
19. For achiral trisoxazolines, see: (j) Capriati, V.; Florio, S.; Luisi, R.; Rocchetti, M. T. J. Org. Chem. 2002, 67, 759.
20. (k) Bellemin-Laponnaz, S.; Gade, L. H. Chem. Commun. 2002, 1286.
21. (l) Sorrell, T. N.; Pigge, F. C.; White, P. S. Inorg. Chim. Acta 1993, 210, 87.
22. (a) Kim, S.-G.; Kim, K.-H.; Kim, Y. K.; Shin, S. K.; Ahn, K. H. J. Am. Chem. Soc. 2003, 125, 13819.
23. (b) Ahn, K. H.; Ku, H.-y.; Kim, Y.; Kim, S.-G.; Kim, Y. K.; Son, H. S.; Ku, J. K. Org. Lett. 2003, 5, 1419.
24. (c) Kim, S.-G.; Kim, K.-H.; Jung, J.; Shin, S. K.; Ahn, K. H. J. Am. Chem. Soc. 2002, 124, 591.
25. (d) Kim, S.-G.; Ahn, K. H. Chem. Eur. J. 2000, 6, 3399.
26. (e) Ahn, K. H.; Kim, S.-G.; Jung, J.; Kim, K.-H.; Kim, J.; Chin, J.; Kim, K. Chem. Lett. 2000, 170.
27. 3-symmetric chiral ligands in asymmetric catalysis, see: Moberg, C. Angew. Chem., Int. Ed. 1998, 37, 248.
28. (a) Zhou, J.; Tang, Y. J. Am. Chem. Soc. 2002, 124, 9030.
29. (b). Zhou, J.; Ye, M.-C.; Huang, Z.-Z. Tang, Y. J. Org. Chem. 2004, 69, 1309.
30. (c) Zhou, J.; Ye, M.-C.; Tang, Y. J. Comb. Chem. 2004, 6, 301.
31. (d) Zhou, J.; Tang, Y. Chem. Commn. 2004, 432.
32. (a) Zhou, J.; Tang, Y. Org. Biomol. Chem. 2004, 2, 429.
33. (b) Huang, Z.-Z.; Kang, Y.-B.; Zhou, J.; Ye, M.-C.; Tang, Y. Org. Lett. 2004, 6, 1677.
34. (c) Ye, M.-C.; Zhou, J.; Huang, Z.-Z. Tang, Y. Chem. Commun. 2003, 2554.
35. Denmark, S. E.; Stiff, C. M. J. Org. Chem. 2000, 65, 5875.
36. (a) Musser, J. H.; Kubrak, D. M.; Chang, J.; Dizio, S. M.; Hite, M.; Hand, J. M.; Lewis, A. J. J. Med. Chem. 1987, 30, 400.
37. (b) Breton, P.; André-Barrés, C.; Langlois, Y. Synth. Commun. 1992, 22, 2543.
38. (c) Sudo, A.; Hashimoto, Y.; Kimoto, H.; Hayashi, K.; Saigo, K. Tetrahadron: Asymmetry 1994, 5, 1333.
39. No desired product was isolated when 2-chloromethyl-2-oxazoline without substitute was used.