Highly enantioselective cyanosilylation of aldehydes catalyzed by novel β-amino alcohol-titanium complexes

Journal of Organic Chemistry

Volumn 69, Issue 23, 2004, Pages 7910-7913

  Li, Yan ^a   He, Bin ^a   Qin, Bo ^a   Feng, Xiaoming ^a   Zhang, Guolin ^a,b  

^a SICHUAN UNIVERSITY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINO ACIDS; AROMATIC COMPOUNDS; CATALYST SELECTIVITY; CATALYSTS; ETHERS; TITANIUM COMPOUNDS;

ALIPATIC ALDEHYDES; CYANOSILYLATION; ENANTIOSELECTIVITY;

ALDEHYDES;

ALDEHYDE; AMINOALCOHOL; CYANOHYDRIN; TITANIUM DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CONJUGATION; ENANTIOSELECTIVITY; SILYLATION;

EID: 8644289262     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0488356     Document Type: Article

References (62)

1. (a) North, M. Synlett 1993, 807-820.
2. (b) Effenberger, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1555-1564.
3. (c) Gregory, R. J. H. Chem. Rev. 1999, 99, 3649-3682.
4. (d) North, M. Tetrahedron: Asymmetry 2003, 14, 147-176.
5. (a) Kanerva, L. T. Acta Chem. Scand. 1998, 50, 234-242.
6. (b) Effenberger, B. F.; Ziegler, T.; Förster S. Angew. Chem., Int. Ed. Engl. 1987, 26, 458-460.
7. (c) Niedermeyer, U.; Kula, M.-R. Angew. Chem., Int. Ed. Engl. 1980, 29, 386-387.
8. (d) Han, S.; Chen, P.; Lin, G.; Huang, H.; Li, Z. Tetrahedron: Asymmetry 2001, 12, 843-846.
9. (e) Brussee, J.; Ross, E. C.; Vander, A. G. Tetrahedron Lett. 1988, 29, 4485-4488.
10. (a) Danda, H. Bull. Chem. Soc. Jpn. 1991, 64, 3743-3745.
11. (b) Hogg, D. J. P.; North, M. Tetrahedron 1993, 49, 1079-1090.
12. (c) Gallant, D.; Coussens, B.; Maten, T. v. d.; Vries, J. G.; Vries, N. K. Tetrahedron: Asymmetry 1992, 3, 401-414.
13. (d) Nitta, H.; Yu, D.; Kudo, M.; Mori, A.; Inoie, S. J. Am. Chem. Soc. 1992, 114, 7969-7975.
14. Bolm, C.; Müller, P. Tetrahedron Lett. 1995, 36, 1625-1628.
15. Brunel, J.-M.; Legrand, O.; Buono, G. Tetrahedron: Asymmetry 1999, 10, 1979-1984.
16. (a) Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229-6232.
17. (b) Sellner, H.; Faber, C.; Rheiner, P. B.; Seebach, D. Chem. Eur. J. 2000, 6, 3692-3705.
18. (c) Tian, J.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2002, 41, 3636-3638.
19. (d) Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989-1999.
20. (e) Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 2641-2642.
21. (f) Hamashima, Y.; Sawada, D.; Nogami, H.; Kanai, M.; Shibasaki, M. Tetrahedron 2001, 57, 805-814.
22. (g) Casas, J.; Najera, C.; Sansano, J. M.; Saa, J. M. Org. Lett. 2002, 4, 2589-2592.
23. (h) Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131-2132.
24. (i) Holmes, I. P.; Kagan, H. B. Tetrahedron Lett. 2000, 41, 7453-7456.
25. (a) Ooi, T.; Miura, T.; Takaya, K.; Ichikawa, H.; Maruoka, K. Tetrahedron 2001, 57, 867-873.
26. (b) Minamikawa, H.; Hayakawa, S.; Yamada, T.; Iwasawa, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1988, 61, 4379-4383.
27. (c) Narasaka, K.; Yamada, T.; Minamikawa, H. Chem. Lett. 1987, 2073-2076.
28. (a) Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001-4004.
29. (b) Abiko, A.; Wang, G.-q. J. Org. Chem. 1998, 61, 2264-2265.
30. (c) Abiko, A.; Wang, G.-q. Tetrahedron 1998, 54, 11405-11420.
31. (d) Kanai, M.; Hamashima, Y.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 2405-2409.
32. (e) Gallant, D.; Stanssens, D.; de Vries, J. G. Tetrahedron: Asymmetry 1993, 4, 185-188.
33. (f) Iovel, I.; Popelia, Y.; Fleisher, M.; Lukevics, E. Tetrahedron: Asymmetry 1997, 8, 1279-1282.
34. (g) Aspinall, H. C.; Greeves, N.; Smith, P. M. Tetrahedron Lett. 1999, 40, 1763-1766.
35. (h) Yang, W.-B.; Fang, J.-M. J. Org. Chem. 1998, 63, 1356-1359.
36. (i) Hwang, C.-D.; Hwang, D.-R.; Uang, B.-J. J. Org. Chem. 1998, 63, 6762-6763.
37. (j) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8106-8107.
38. (a) Hayashi, M.; Miyamoto, Y.; Inoue, T.; Oguni, N. J. Org. Chem. 1993, 58, 1515-1522.
39. (b) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385-4398.
40. (a) Jiang, Y.; Zhou, X.; Hu, W.; Wu, L.; Mi, A. Tetrahedron: Asymmetry 1995, 6, 405-408.
41. (b) Jiang, Y.; Zhou, X.; Hu, W.; Li, Z.; Mi, A. Tetrahedron: Asymmetry 1995, 6, 2915-2916.
42. (c) Flores-Lopéz, L. Z.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Organometallics 2000, 19, 2153-2160.
43. (d) Gama, A.; Flores-Lopéz, L. Z.; Aguirre, G.; Parra-Hake, M.; Somanathan, R.; Walsh, P. J. Tetrahedron: Asymmetry 2002, 13, 149-154.
44. (e) Jiang, Y.; Gong, L.; Feng, X.; Hu, W.; Pan, W.; Li, Z.; Mi, A. Tetrahedron 1997, 53, 14327-14338.
45. (f) Belokon, Y.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orlova, S.; Tararov, V.; Yashkina, L. Tetrahedron: Asymmetry 1996, 7, 851-855.
46. (g) Belokon, Y.; Flego, M.; Ikonnikov, N.; Moscalenko, M.; North, M.; Orizu, C.; Tararov, V.; Tasinazzo, M. J. Chem. Soc., Perkin Trans. 1 1997, 1293-1296.
47. (h) Belokon, Y. N.; North, M.; Parsons, T. Org. Lett. 2000, 2, 1617-1619.
48. (i) Liang, S.; Bu, X. R. J. Org. Chem. 2002, 67, 2702-2704.
49. (j) Tararov, V. I.; Hibbs, D. E.; Hursthouse, M. B.; Ikonnikov, N. S.; Malik, K. M. A.; North, M.; Orizu, C.; Belokon', Y. N. Chem. Commun. 1998, 387-388.
50. (k) Belokon, Y. N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N. S.; Khrustalev, V. N.; Larichev, V. S.; Moscalenko, M. A.; North, M.; Orizu, C.; Tararov, V. I.; Tasinazzo, M.; Timofeeva, G. I.; Yashkina, L. V. J. Am. Chem. Soc. 1999, 121, 3968-3973.
51. (l) Belokon, Y. N.; Green, B.; Ikonnikov, N. S.; Larichev, V. S.; Lokshin, B. V.; Moscalenko, M. A.; North, M.; Orizu, C.; Peregudov, A. S.; Timofeeva, G. I. Eur. J. Org. Chem. 2000, 2655-2661.
52. (m) Belokon, Y. N.; Gutnov, A. V.; Moskalenko, M. A.; Yashkina, L. V.; Lesovoy, D. E.; Ikonnikov, N. S.; Larichev, V. S.; North, M. Chem. Commun. 2002, 244-245.
53. (n) Belokon, Y. N.; Carta P.; Gutnov, A. V.; Maleev, V. I.; Moskalenko, M. A.; Yashkina, L. V.; Ikonnikov, N. S.; Voskoboev, N.; Khrustalev, V. N.; North, M. Helv. Chim. Acta 2002, 85, 3301-3312.
54. (o) Reference deleted in proof.
55. (p) Holmes, I. P.; Kagan, H. B. Tetrahedron Lett. 2000, 41, 7457-7460.
56. (q) Belokon, Y.; Moscalenko, M.; Ikonnikov, N.; Yashkina, L.; Antonov, D.; Vorontsov, E.; Rozenberg, V. Tetrahedron: Asymmetry 1997, 8, 3245-3250.
57. (r) Zhou, X.-G.; Huang, J.-S.; Ko, P.-H.; Cheung, K.-K.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1999, 3303-3309.
58. (s) Yang, Z.; Zhou, Z.; Tang, C. Synth. Commun. 2001, 31, 3031-3036.
59. (t) Yang, Z.-H.; Wang, L.-X.; Zhou, Z.-H.; Zhou, Q.-L.; Tang, C.-C. Tetrahedron: Asymmetry 2001, 12, 1579-1582.
60. You, J.-S.; Gau, H.-M.; Choi, M. C. K. Chem. Commun. 2000, 1963-1964.
61. Mansawat, W.; Bhanthumnavin, W.; Vilaivan, T. Tetrahedron Lett. 2003, 44, 3805-3808.
62. Suwa, T.; Sugiyama, E.; Shibata, I.; Baba, A. Synthesis 2000, 789-800.