Asymmetric Catalytic Hydrosilylation of Ketones with Triethoxysilane Using a Chiral Binaphthol-Titanium Complex

Synlett

Volumn 1996, Issue 12, 1996, Pages 1229-1230

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

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002826596     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5726     Document Type: Article

References (19)

1. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, Inc: New York, 1994.
2. (b) Catalytic Asymmetric Synthesis; Ojima, I. Ed.; VCH: New York, 1993.
3. Reviews: (a) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255. (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.
4. Reviews: (a) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255. (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.
5. A dimeric structure has been reported for the crystal structure of complex B: Martin, C. A. Ph. D. Thesis, MIT, 1988.
6. Kitamoto, D.; Imma, H.; Nakai, T. Tetrahedron Lett. 1995, 36, 1861.
7. Review: Nishiyama, H.; Itoh, K. J. Synth. Org. Chem., Jpn. 1995, 53, 503. For more recent works, see: (a) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (b) Uemura, S.; Nishibayashi, Y.; Segawa, K.; Singh, J. D.; Fukuzawa, S.; Ohe, K. Organometallics 1996, 15, 370. (c) Nishibayashi, Y.; Segawa, K.; Hiroya, H.; Ohe, K.; Uemura, S. Chem. Commun. 1996, 847.
8. Review: Nishiyama, H.; Itoh, K. J. Synth. Org. Chem., Jpn. 1995, 53, 503. For more recent works, see: (a) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (b) Uemura, S.; Nishibayashi, Y.; Segawa, K.; Singh, J. D.; Fukuzawa, S.; Ohe, K. Organometallics 1996, 15, 370. (c) Nishibayashi, Y.; Segawa, K.; Hiroya, H.; Ohe, K.; Uemura, S. Chem. Commun. 1996, 847.
9. Review: Nishiyama, H.; Itoh, K. J. Synth. Org. Chem., Jpn. 1995, 53, 503. For more recent works, see: (a) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (b) Uemura, S.; Nishibayashi, Y.; Segawa, K.; Singh, J. D.; Fukuzawa, S.; Ohe, K. Organometallics 1996, 15, 370. (c) Nishibayashi, Y.; Segawa, K.; Hiroya, H.; Ohe, K.; Uemura, S. Chem. Commun. 1996, 847.
10. Review: Nishiyama, H.; Itoh, K. J. Synth. Org. Chem., Jpn. 1995, 53, 503. For more recent works, see: (a) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. (b) Uemura, S.; Nishibayashi, Y.; Segawa, K.; Singh, J. D.; Fukuzawa, S.; Ohe, K. Organometallics 1996, 15, 370. (c) Nishibayashi, Y.; Segawa, K.; Hiroya, H.; Ohe, K.; Uemura, S. Chem. Commun. 1996, 847.
11. Halterman, R. L.; Ramsey, T. M.; Chen, Z. J. Org. Chem. 1994, 59, 2642. In their work, chiral titanocene dichlorides have been employed as precatalysts in the hydrosilylation with triethoxysilane to give low %ee's (up to 40%).
12. Carter, M. B.; Schiøtt, B.; Gutiérrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667. In their work, remarkably high %ee's (up to 97%) have been achieved by using the BINOL-derived chiral titanocene as a precatalyst and polymethylhydrosiloxane as a hydrosilylating agent.
13. Berk, S. C.; Buchwald, S. L. J. Org. Chem. 1992 , 57, 3751.
14. In any ligand exchange reactions involved in this Scheme, it is reasonably postulated that only the alkoxy ligand is exchanged, while the BINOL ligand is retained due to its stronger coordinating ability.
15. 1H NMR analysis of the corresponding MTPA ester.
16. Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. For recent examples, see: (a) Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. (b) Soai, K.; Shibata, T.; Morioka, H.; Choji. K. Nature 1995, 35, 1657. (c) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem. Int. Ed. Engl. 1996, 35, 1657.
17. Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. For recent examples, see: (a) Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. (b) Soai, K.; Shibata, T.; Morioka, H.; Choji. K. Nature 1995, 35, 1657. (c) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem. Int. Ed. Engl. 1996, 35, 1657.
18. Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. For recent examples, see: (a) Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. (b) Soai, K.; Shibata, T.; Morioka, H.; Choji. K. Nature 1995, 35, 1657. (c) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem. Int. Ed. Engl. 1996, 35, 1657.
19. Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265. For recent examples, see: (a) Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740. (b) Soai, K.; Shibata, T.; Morioka, H.; Choji. K. Nature 1995, 35, 1657. (c) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem. Int. Ed. Engl. 1996, 35, 1657.