Chiral Oxazolinylferrocene-Phosphine Hybrid Ligand for the Asymmetric Hydrosilylation of Ketones

Organometallics

Volumn 14, Issue 12, 1995, Pages 5486-5487

  Nishibayashi, Yoshiaki ^a   Segawa, Kyohei ^a   Ohe, Kouichi ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000706955     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00012a012     Document Type: Article

References (19)

1. For reviews, see: (a) Ojima, I., Ed. Catalytic Asymmetric Synthesis; VCH: New York, 1993.
2. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
3. For examples: (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675.
4. Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856.
5. Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
6. Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C. P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
7. Noyori, R.; Tomino, I.; Tanimoto, Y. J. Am. Chem. Soc. 1979, 101, 3129.
8. Dumont, W.; Poulin, J. C.; Dang, T.-P.; Kagan, H. B. J. Am. Chem. Soc. 1973, 95, 8295.
9. For example: Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 867.
10. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79.
11. Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74.
12. Sammakia et al. have also reported the highly diastereoselective ortho-lithiation of chiral oxazolinylferrocenes: Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10.
13. For example: (a) Brunner, H.; Becker, R.; Roepl, G. Organometallics 1984, 3, 1354.
14. Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500.
15. Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K. J. Org. Chem. 1992, 57, 4306.
16. With the chiral aminophosphine ligand AMPHOS, 72% ee was obtained in the hydrosilylation of tert-butyl methyl ketone: Payne, N. C.; Stephan, D. W. Inorg. Chem. 1982, 21, 182.
17. With the trans-chelating diphosphine n-BuTRAP, 80% ee was obtained in the hydrosilylation of cyclohexyl methyl ketone: Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111.
18. The enantioselectivity of the Ir(I)-catalyzed hydrosilylation of acetophenone was up to 32% ee: (a) Faller, J. W.; Chase, K. J. Organometallics 1994, 13, 989.
19. Kinting, A.; Kreuzfeld, H.-J.; Abicht, H.P. J. Organomet Chem. 1989, 370, 343.