Titanium and ruthenium binaphthyl Schiff base complexes as catalysts for asymmetric trimethylsilylcyanation of aldehydes

Abstract

Investigations on the catalytic behaviour of titanium complexes formed in situ from Ti(OPrⁱ)₄ and a variety of Schiff bases, mainly the binaphthyl derivatives 2,2′-bis(3-R¹-5-R²-2-hydroxybenzylideneamino)-1,1′-binaphthyl, toward the asymmetric trimethylsilylcyanation of some aromatic and aliphatic aldehydes demonstrated that the titanium complex of the binaphthyl Schiff base with R¹ = R² = Bu^t is one of the best catalysts for such a process, with an enantiomeric excess (e.e.) as high as 96% obtained for m-tolualdehyde. Crystal structure determination of a nitrosylruthenium complex, [Ru^II(L)(NO)Cl] (L is the dianion of the binaphthyl Schiff base with R¹ = R² = Cl), revealed that the complex assumes a cis-β configuration with the binaphthyl moiety having a dihedral angle of 70.2°. After treatment with AgPF₆, the ruthenium complex also exhibited a good catalytic property for the trimethylsilylcyanation of benzaldehyde albeit with a lower e.e. (24%).

References

1. M. North, Synlett, 1993, 807.
2. F. Effenberger, Angew. Chem., Int. Ed. Engl., 1994, 33, 1555.
3. C. G. Kruse, in Chirality in Industry, eds. A. N. Collins, G. N. Sheldrake and J. Crosby, Wiley, Chichester, 1992, ch. 14.
4. M. T. Reetz, S.-H. Kyung, C. Bolm and T. Zierke, Chem. Ind., 1986, 824.
5. K. Narasaka, T. Yamada and H. Minamikawa, Chem. Lett., 1987, 2073.
6. H. Minamikawa, S. Hayakawa, T. Yamada, N. Iwasawa and K. Narasaka, Bull. Chem. Soc. Jpn., 1988, 61, 4379.
7. M. Hayashi, T. Matsuda and N. Oguni, J. Chem. Soc., Chem. Commun., 1990, 1364.
8. M. Hayashi, Y. Miyamoto, T. Inoue and N. Oguni, J. Chem. Soc., Chem. Commun., 1991, 1752.
9. M. Hayashi, Y. Miyamoto, T. Inoue and N. Oguni, J. Org. Chem., 1993, 58, 1515.
10. Y.-Z. Jiang, X.-G. Zhou, W.-H. Hu, L.-J. Wu and A.-Q. Mi, Tetrahedron: Asymmetry, 1995, 6, 405.
11. Y. Belokon, N. Ikonnikov, M. Moscalenko, M. North, S. Orlova, V. Tararov and L. Yashkina, Tetrahedron: Asymmetry, 1996, 7, 851.
12. W.-D. Pan, X.-M. Feng, L.-Z. Gong, W.-H. Hu, Z. Li, A.-Q. Mi and Y.-Z. Jiang, Synlett, 1996, 337.
13. Y. Belokon, M. Moscalenko, N. Ikonnikov, L. Yashkina, D. Antonov, E. Vorontsov and V. Rozenberg, Tetrahedron: Asymmetry, 1997, 8, 3245.
14. Y. Belokon, M. Flego, N. Ikonnikov, M. Moscalenko, M. North, C. Orizu, V. Tararov and M. Tasinazzo, J. Chem. Soc., Perkin Trans. 1, 1997, 1293.
15. V. I. Tararov, D. E. Hibbs, M. B. Hursthouse, N. S. Ikonnikov, K. M. A. Malik, M. North, C. Orizu and Y. N. Belokon, Chem. Commun., 1998, 387.
16. G.-F. Zi and C.-L. Yin, J. Mol. Catal. A: Chemical, 1998, 132, L1.
17. M. Mori, H. Imma and T. Nakai, Tetrahedron Lett., 1997, 38, 6229.
18. C.-D. Hwang, D.-R. Hwang and B.-J. Uang, J. Org. Chem., 1998, 63, 6762.
19. E. J. Corey and Z. Wang, Tetrahedron Lett., 1993, 34, 4001.
20. C.-T. Qian, C.-J. Zhu and T.-S. Huang, J. Chem. Soc., Perkin Trans. 1, 1998, 2131.
21. A. Abiko and G.-Q. Wang, J. Org. Chem., 1996, 61, 2264.
22. R. Noyori, in Stereocontrolled Organic Synthesis, ed. B. M. Trost, Blackwell Scientific Publications, Oxford, 1994, p. 1.
23. C. Rosini, L. Franzini, A. Raffaelli and P. Salvadori, Synthesis, 1992, 503.
24. M.-C. Cheng, M. C.-W. Chan, S.-M. Peng, K.-K. Cheung and C.-M. Che, J. Chem. Soc., Dalton Trans., 1997, 3479.
25. C.-W. Ho, W.-C. Cheng, M.-C. Cheng, S.-M. Peng, K.-F. Cheng and C.-M. Che, J. Chem. Soc., Dalton Trans., 1996, 405.
26. S. Miyano, M. Nawa, A. Mori and H. Hashimoto, Bull. Chem. Soc. Jpn., 1984, 57, 2171.
27. K. Bernardo, A. Robert, F. Dahan and B. Meunier, New J. Chem., 1995, 19, 129.
28. K. Bernardo, S. Leppard, A. Robert, G. Commenges, F. Dahan and B. Meunier, Inorg. Chem., 1996, 35, 387.
29. E. M. Carreira, R. A. Singer and W. Lee, J. Am. Chem. Soc., 1994, 116, 8837.
30. J. J. Levison and S. D. Robinson, J. Chem. Soc. A, 1970, 2947.
31. D. J. Cram, R. C. Helgeson, S. C. Peacock, L. J. Kaplan, L. A. Domeier, P. Moreau, K. Koga, J. M. Mayer, Y. Chao, M. G. Siegel, D. H. Hoffman and G. D. Y. Sogah, J. Org. Chem., 1978, 43, 1930.
32. B. R. Matthews, W. R. Jackson, G. S. Jayatilake, C. Wilshire and H. A. Jacobs, Aust. J. Chem., 1988, 41, 1697.
33. E. M. Carreira, W. Lee and R. A. Singer, J. Am. Chem. Soc., 1995, 117, 3649.
34. R. A. Singer and E. M. Carreira, J. Am. Chem. Soc., 1995, 117, 12360.
35. W. Odenkirk, A. L. Rheingold and B. Bosnich, J. Am. Chem. Soc., 1992, 114, 6392.