Practical synthesis of chiral ligands for catalytic enantioselective cyanosilylation of ketones and ketoimines

Journal of Organic Chemistry

Volumn 69, Issue 18, 2004, Pages 6128-6130

  Kato, Nobuki ^a,b   Tomita, Daisuke ^a   Maki, Keisuke ^a   Kanai, Motomu ^a,b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETOIMINES; LIGANDS;

CATALYSIS; SYNTHESIS (CHEMICAL);

KETONES;

2 (DIPHENYLPHOSPHINOYLMETHYL)TETRAHYDROPYRAN 3,4 DIOL; 4 (DIPHENYLPHOSPHINOYLMETHYL)TETRAHYDRO 1,3,2 DIOXATHIAZOLO[4,5 C]PYRAN 2,2 DIOXIDE; 6 (DIPHENYLPHOSPHINOYLMETHYL) 3,6 DIHYDRO 2H PYRAN; CATECHOL; IMINE; KETOIMINE; KETONE; LIGAND; NITRILE; PYRAN DERIVATIVE; TOLUENE 4 SULFONIC ACID 5,6 DIHYDRO 2H PYRAN 2 YL METHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 4344651527     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049258o     Document Type: Article

References (37)

1. (a) Hamashima, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 7412.
2. (b) Hamashima, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 691.
3. (c) Fujii, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733.
4. (d) Yabu, K.; Masumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908.
5. (e) Yabu, K.; Masumoto, S.; Kanai, M.; Curran, D. P.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 2923.
6. (f) Masumoto, S.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 8647.
7. (g) Yabu, K.; Masumoto, S.; Kanai, M.; Shibasaki, M. Heterocycles 2003, 59, 369.
8. For examples of catalytic enantioselective cyanosilylation of ketones from other groups, see: (a) Belokoń, Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Tararov, V. I. Tetrahedron Lett. 1999, 38, 6669.
9. (b) Belokoń, 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.
10. (c) Belokoń, 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.
11. (d) Belokoń, Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Parsons, T.; Tararov, V. I. Tetrahedron 2001, 57, 771.
12. (e) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2001, 123, 6195.
13. (f) Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2003, 125, 9900.
14. (g) Deng, H.; Isler, M. P.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2002, 41, 1009.
15. (h) Chen, F.; Feng, Z.; Qin, B.; Zhang, G.; Jiang, Y. Org. Lett. 2003, 5, 949.
16. (i) Shen, Y.; Feng, X.; Li, Y.; Zhang, G.; Jiang, Y. Eur. J. Org. Chem. 2004, 129.
17. (a) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634.
18. (b) Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3147.
19. (c) Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3153.
20. For examples of catalytic enantioselective Strecker reaction of ketoimines from other groups, see: (a) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
21. (b) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
22. (c) Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Vallée, Y. Tetrahedron: Asymmetry 2001, 12, 1147.
23. For a recent review of the catalytic enantioselective Strecker reaction of ketoimines, see: (d) Spino, C. Angew. Chem. 2004, 43, 1764.
24. With use of 1b-Ti (1:1) complex at 0 °C, (R)-amidonitriles are obtained predominantly, despite with low enantioselectivity (up to 12% ee).
25. Masumoto, S.; Yabu, K.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 2919.
26. Trost, B. M.; Brown, B. S.; McEachern, E. J.; Kuhn, O. Chem. Eur. J. 2003, 9, 4442.
27. In the original report, 1.1 equiv of 3 were used for this reaction (82%, 90% ee). With 1.5 equiv of 3, the yield was improved while maintaining excellent enantioselectivity (95%, 89% ee).
28. (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856.
29. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
30. For recent reviews of ring-closing metathesis, see: (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
31. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
32. (e) Jorgensen, M.; Hadwiger, P.; Madsen, R.; Stütz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 565.
33. (a) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
34. (b) Lohray, B. B. Synthesis 1992, 1035.
35. (a) Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117, 10143.
36. (b) Pettit, G. R.; Melody, N.; Herald, D. L. J. Org. Chem. 2001, 66, 2583.
37. In the previous synthetic route, monomethylated catechol derivatives were used for the introduction of a catechol moiety.