Asymmetric catalytic cyanosilylation of aldehydes using a chiral binaphthol-titanium complex

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6229-6232

  Mori, Maki ^a   Imma, Hironori ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; FUNCTIONAL GROUP; TITANIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOMER; REACTION ANALYSIS; TEMPERATURE;

EID: 0030756043     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01432-9     Document Type: Article

References (16)

1. Reviews: (a) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255-265. (b) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press, Inc: London, 1995; 1, p 123-149.
2. Reviews: (a) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255-265. (b) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press, Inc: London, 1995; 1, p 123-149.
3. A dimeric structure has been reported for the crystal structure of complex B: Martin, C. A. Ph. D. Thesis, MIT, 1988.
4. Kitamoto, D.; Imma, H.; Nakai, T. Tetrahedron Lett. 1995, 36, 1861-1864.
5. Imma, H.; Mori, M.; Nakai, T. Synlett 1996, 12, 1229-1230.
6. Reviews: North, M. Synlett 1993, 807-820. For the asymmetric catalytic cyanosilylations with TMSCN using chiral Ti complexes in particular, see: (a) Minamikawa, H.; Hayakawa, S.; Yamada, T.; Iwasawa, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1988, 61, 4379-4383. (b) Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc. Perkin Trans. 1 1992, 3135-3140. (c) Hayashi, M.; Tanaka, K.; Oguni, N. Tetrahedron 1994, 50, 4385-4398. (d) Bolm, C.; Müller, P. Tetrahedron Lett. 1995, 36, 1625-1628.
7. Reviews: North, M. Synlett 1993, 807-820. For the asymmetric catalytic cyanosilylations with TMSCN using chiral Ti complexes in particular, see: (a) Minamikawa, H.; Hayakawa, S.; Yamada, T.; Iwasawa, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1988, 61, 4379-4383. (b) Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc. Perkin Trans. 1 1992, 3135-3140. (c) Hayashi, M.; Tanaka, K.; Oguni, N. Tetrahedron 1994, 50, 4385-4398. (d) Bolm, C.; Müller, P. Tetrahedron Lett. 1995, 36, 1625-1628.
8. Reviews: North, M. Synlett 1993, 807-820. For the asymmetric catalytic cyanosilylations with TMSCN using chiral Ti complexes in particular, see: (a) Minamikawa, H.; Hayakawa, S.; Yamada, T.; Iwasawa, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1988, 61, 4379-4383. (b) Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc. Perkin Trans. 1 1992, 3135-3140. (c) Hayashi, M.; Tanaka, K.; Oguni, N. Tetrahedron 1994, 50, 4385-4398. (d) Bolm, C.; Müller, P. Tetrahedron Lett. 1995, 36, 1625-1628.
9. Reviews: North, M. Synlett 1993, 807-820. For the asymmetric catalytic cyanosilylations with TMSCN using chiral Ti complexes in particular, see: (a) Minamikawa, H.; Hayakawa, S.; Yamada, T.; Iwasawa, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1988, 61, 4379-4383. (b) Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc. Perkin Trans. 1 1992, 3135-3140. (c) Hayashi, M.; Tanaka, K.; Oguni, N. Tetrahedron 1994, 50, 4385-4398. (d) Bolm, C.; Müller, P. Tetrahedron Lett. 1995, 36, 1625-1628.
10. Reviews: North, M. Synlett 1993, 807-820. For the asymmetric catalytic cyanosilylations with TMSCN using chiral Ti complexes in particular, see: (a) Minamikawa, H.; Hayakawa, S.; Yamada, T.; Iwasawa, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1988, 61, 4379-4383. (b) Hayashi, M.; Matsuda, T.; Oguni, N. J. Chem. Soc. Perkin Trans. 1 1992, 3135-3140. (c) Hayashi, M.; Tanaka, K.; Oguni, N. Tetrahedron 1994, 50, 4385-4398. (d) Bolm, C.; Müller, P. Tetrahedron Lett. 1995, 36, 1625-1628.
11. 4), 43% ee(S).
12. It should be noted that a similar use of 6, 6′-dibromo-, 3, 3′-dibromo-, 3, 3′-diphenyl-, or 3, 3′-dimethyl-BINOL in place of BINOL was found to provide a much lower % ee. These BINOL derivatives were prepared according to the literature procedures: Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253-2256.
13. The chiral complex F, if it acts as the catalyst, should provide a different % ee from that of complex E, thus the overall %ee depending, more or less, on % conversion.
14. For the concept of "enantioselective autoinduction", see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265-7266. For a remarkable example in the catalytic asymmetric hydrocyanation of aldehydes with HCN, see: Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740-6741.
15. For the concept of "enantioselective autoinduction", see: Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265-7266. For a remarkable example in the catalytic asymmetric hydrocyanation of aldehydes with HCN, see: Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740-6741.
16. Both Narasaka et al. (ref. 5a) and Oguni et al. (ref. 5b) have reported that the cyanosilylations of aromatic aldehydes give higher % ee's than those of aliphatic aldehydes.