Ruthenium-catalyzed asymmetric hydrosilylation of ketones and imine

Organometallics

Volumn 17, Issue 16, 1998, Pages 3420-3422

  Nishibayashi, Yoshiaki ^a   Takei, Izuru ^a   Uemura, Sakae ^b   Hidai, Masanobu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001343261     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980399o     Document Type: Article

References (30)

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2. For reviews, see: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993. (b) Brunner, H.; Zettimeier, W. Handbook of Enantioselective Catalysis with Transition Metal Compounds; VCH: Weinheim, Germany, 1993. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
3. For reviews, see: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993. (b) Brunner, H.; Zettimeier, W. Handbook of Enantioselective Catalysis with Transition Metal Compounds; VCH: Weinheim, Germany, 1993. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
4. For recent examples, see: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. (b) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. (c) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503-2506. (d) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. (e) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599-1602. (f) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807. (g) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398-409.
5. For recent examples, see: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. (b) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. (c) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503-2506. (d) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. (e) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599-1602. (f) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807. (g) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398-409.
6. For recent examples, see: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. (b) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. (c) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503-2506. (d) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. (e) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599-1602. (f) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807. (g) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398-409.
7. For recent examples, see: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. (b) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. (c) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503-2506. (d) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. (e) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599-1602. (f) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807. (g) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398-409.
8. For recent examples, see: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. (b) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. (c) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503-2506. (d) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. (e) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599-1602. (f) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807. (g) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398-409.
9. For recent examples, see: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. (b) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. (c) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503-2506. (d) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. (e) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599-1602. (f) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807. (g) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398-409.
10. For recent examples, see: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. (b) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. (c) Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503-2506. (d) Newman, L. M.; Williams, J. M. J.; McCague, R.; Potter, G. A. Tetrahedron: Asymmetry 1996, 7, 1597-1598. (e) Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599-1602. (f) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807. (g) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398-409.
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19. Ketones: Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667-11670.
20. Imines: (a) Verdaguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784-6785. (b) Verdaguer, X.; Lange, U. E. W.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 1103-1106.
21. Imines: (a) Verdaguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784-6785. (b) Verdaguer, X.; Lange, U. E. W.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1998, 37, 1103-1106.
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27. w = 0.043) for 4264 unique reflections with I > 3σ(I).
28. 4. For the GLC analyses, naphthalene was added as an internal standard. For isolation, the extract was concentrated under reduced pressure by an aspirator and then distilled under vacuum by Kugelrohr to give the corresponding alcohol together with the unreacted starting ketone. Dimethoxydiphenylsilane was left in the residue. The ee value and the configuration of the alcohol were determined by GLC on a cyclodextrin phase (Chiraldex GT-A, 30 m).
29. Several studies have demonstrated that substituted 2-aryl-1-pyrrolines may have benefical effects in the treatment of Parkinson's disease, Alzheimer's disease, attention deficit hyperactivity disorder, Tourette's syndrome, and schizophrenia. For a recent example, see: Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109-1118 and references therein.
30. During the preparation of this manuscript, the ruthenium-catalyzed asymmetric hydrosilylation of alkyl aryl ketones using tridentate ligands was reported. However, the enantioselectivities were moderate (up to 66% ee); Zhu, G.; Terry M.; Zhang, X. J. Organomet. Chem. 1997, 547, 97-101.