[Ru((R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl)(H)-(MeCN) (THF)2](BF4), a catalyst system for hydrosilylation of ketones and for isomerization, intramolecular hydrosilylation, and hydrogenation of olefins

Organometallics

Volumn 15, Issue 18, 1996, Pages 3782-3784

  Wiles, Jason A ^a   Lee, Christopher E ^a   McDonald, Robert ^a,b   Bergens, Steven H ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b Structure Determination Laboratory

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000666417     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9603979     Document Type: Article

References (47)

1. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
2. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
3. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
4. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
5. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
6. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
7. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
8. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
9. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
10. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
11. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
12. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
13. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
14. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
15. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
16. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
17. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
18. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
19. For excellent reviews on the discovery literature in this area see: (a) Takaya, H.; Ohta, T.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; p 1. (b) Noyori, R. In Aymmetric Catalysis in Organic Synthesis; Wiley-Interstience: New York, 1994; p 16. For recent examples see: (c) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1993, 115, 144. (d) Mezzetti, A.; Costella, L.; Del Zotto, A.; Rigo, P. Gazz. Chim. Ital. 1993, 123, 155. (e) Hoke, J. B.; Hollis, L. S.; Stern, E. W. J. Organomet. Chem. 1993, 455, 193. (f) Manimaran, T.; Wu, T.-C.; Kolbucar, W. D.; Kolich, C. H.; Stahly, G. P.; Fronczek, F. R.; Watkins, S. E. Organometallics 1993, 12, 1467. (g) Chiba, T.; Miyashita, A.; Nohira, H. Tetrahedron Lett. 1993, 34, 2351. (h) Wan, K.; Davis, M. E. Tetrahedron: Asymmetry 1993, 4, 2461. (i) Chan, A. C. S.; Laneman, S. Inorg. Chim. Acta 1994, 223, 165. (j) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297. (k) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665. (l) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675. (m) Masima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064. (n) Chan, A. C. S.; Chen, C. C.; Yang, T. K.; Huang, J. H.; Lin, Y. C. Inorg. Chim. Acta 1995, 234, 95. (o) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade Tetrahedron Lett. 1995, 36, 2063. (p) Ohkuma, T.; Ooka. H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675. (q) Kitamura, M.; Tokunaga, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2931. (r) Burke, M. J.; Harper, G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423. (s) Genêt, J. P.; Ratovelomanana-Vidal, V.; Caño De Andrade, M. C.; Pfister, X.; Guerreiro, P.; Lenoir, J. Y. Tetrahedron Lett. 1995, 36, 4801.
20. (a) Brown, J. M.; Brunner, H.; Leitner, W.; Rose, M. Tetrahedron: Asymmetry 1991, 2, 331.
21. (b) Saburi, M.; Ohnuki, M.; Ogasawara, M.; Takahashi, T.; Uchida, Y. Tetrahedron Lett. 1992, 33, 5783.
22. (c) Genêt, J.-P.; Ratovelomanana-Vidal, V.; Pinel, C. Synlett 1993, 478.
23. (d) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.
24. We limit our discussion to bis(phosphine) ligands because of the high success obtained with their use in homogeneous catalysis and because, in general, multidentate, chiral ligands are required to obtain high ee values. For examples of high enantioselectivity obtained using monodentate, chiral phosphine ligands see: (a) Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101. For examples of Ru(bis(phosphine))-catalyzed reactions other than hydrogenations, see the following. For isomerization of olefins: (b) Frauenrath, H.; Philipps, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 274. (c) Frauenrath, H.; Kaulard, M. Synlett 1994, 517. For intramolecular hydrosilylation of ketones, (d) Burk, M. J.; Feaster, J. E. Tetrahedron Lett. 1992, 33, 2099. For hydrosilylation of nitrones: (e) Murahashi, S.-I.; Watanabe, S.; Shiota, T. J. Chem. Soc., Chem. Commun. 1994, 725.
25. We limit our discussion to bis(phosphine) ligands because of the high success obtained with their use in homogeneous catalysis and because, in general, multidentate, chiral ligands are required to obtain high ee values. For examples of high enantioselectivity obtained using monodentate, chiral phosphine ligands see: (a) Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101. For examples of Ru(bis(phosphine))-catalyzed reactions other than hydrogenations, see the following. For isomerization of olefins: (b) Frauenrath, H.; Philipps, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 274. (c) Frauenrath, H.; Kaulard, M. Synlett 1994, 517. For intramolecular hydrosilylation of ketones, (d) Burk, M. J.; Feaster, J. E. Tetrahedron Lett. 1992, 33, 2099. For hydrosilylation of nitrones: (e) Murahashi, S.-I.; Watanabe, S.; Shiota, T. J. Chem. Soc., Chem. Commun. 1994, 725.
26. We limit our discussion to bis(phosphine) ligands because of the high success obtained with their use in homogeneous catalysis and because, in general, multidentate, chiral ligands are required to obtain high ee values. For examples of high enantioselectivity obtained using monodentate, chiral phosphine ligands see: (a) Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101. For examples of Ru(bis(phosphine))-catalyzed reactions other than hydrogenations, see the following. For isomerization of olefins: (b) Frauenrath, H.; Philipps, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 274. (c) Frauenrath, H.; Kaulard, M. Synlett 1994, 517. For intramolecular hydrosilylation of ketones, (d) Burk, M. J.; Feaster, J. E. Tetrahedron Lett. 1992, 33, 2099. For hydrosilylation of nitrones: (e) Murahashi, S.-I.; Watanabe, S.; Shiota, T. J. Chem. Soc., Chem. Commun. 1994, 725.
27. We limit our discussion to bis(phosphine) ligands because of the high success obtained with their use in homogeneous catalysis and because, in general, multidentate, chiral ligands are required to obtain high ee values. For examples of high enantioselectivity obtained using monodentate, chiral phosphine ligands see: (a) Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101. For examples of Ru(bis(phosphine))-catalyzed reactions other than hydrogenations, see the following. For isomerization of olefins: (b) Frauenrath, H.; Philipps, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 274. (c) Frauenrath, H.; Kaulard, M. Synlett 1994, 517. For intramolecular hydrosilylation of ketones, (d) Burk, M. J.; Feaster, J. E. Tetrahedron Lett. 1992, 33, 2099. For hydrosilylation of nitrones: (e) Murahashi, S.-I.; Watanabe, S.; Shiota, T. J. Chem. Soc., Chem. Commun. 1994, 725.
28. We limit our discussion to bis(phosphine) ligands because of the high success obtained with their use in homogeneous catalysis and because, in general, multidentate, chiral ligands are required to obtain high ee values. For examples of high enantioselectivity obtained using monodentate, chiral phosphine ligands see: (a) Hayashi, T.; Niizuma, S.; Kamikawa, T.; Suzuki, N.; Uozumi, Y. J. Am. Chem. Soc. 1995, 117, 9101. For examples of Ru(bis(phosphine))-catalyzed reactions other than hydrogenations, see the following. For isomerization of olefins: (b) Frauenrath, H.; Philipps, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 274. (c) Frauenrath, H.; Kaulard, M. Synlett 1994, 517. For intramolecular hydrosilylation of ketones, (d) Burk, M. J.; Feaster, J. E. Tetrahedron Lett. 1992, 33, 2099. For hydrosilylation of nitrones: (e) Murahashi, S.-I.; Watanabe, S.; Shiota, T. J. Chem. Soc., Chem. Commun. 1994, 725.
29. Sun, Y.; LeBlond, C.; Wang, J.; Blackmond, D. G. J. Am. Chem. Soc. 1995, 117, 12647.
30. Schrock, R. R.; Johnson, B. F. G.; Lewis, J. J. Chem. Soc., Dalton Trans. 1974, 951.
31. 1H NMR spectroscopy.
32. 11. We have been unable to separate the two isomers of 1 and confirm that they are diastereomers.
33. 4) is the only detectable species in solution upon hydrogenation of 1 followed by addition of excess acetonitrile.
34. 11, see: Ashworth, T. V.; Nolte, M. J.; Reimann, R. H.; Singleton, E. J. Chem. Soc. Chem. Commun. 1977, 937. Bouachir, F.; Chaudret, B.; Neibecker, D.; Tkatchenko, I. Angew. Chem. 1985, 347. Ashworth, T. V.; Chalmers, A. A.; Liles, D. C.; Meintjies, E.; Singleton, E. Organometallics 1987, 6, 1543.
35. 11, see: Ashworth, T. V.; Nolte, M. J.; Reimann, R. H.; Singleton, E. J. Chem. Soc. Chem. Commun. 1977, 937. Bouachir, F.; Chaudret, B.; Neibecker, D.; Tkatchenko, I. Angew. Chem. 1985, 347. Ashworth, T. V.; Chalmers, A. A.; Liles, D. C.; Meintjies, E.; Singleton, E. Organometallics 1987, 6, 1543.
36. 11, see: Ashworth, T. V.; Nolte, M. J.; Reimann, R. H.; Singleton, E. J. Chem. Soc. Chem. Commun. 1977, 937. Bouachir, F.; Chaudret, B.; Neibecker, D.; Tkatchenko, I. Angew. Chem. 1985, 347. Ashworth, T. V.; Chalmers, A. A.; Liles, D. C.; Meintjies, E.; Singleton, E. Organometallics 1987, 6, 1543.
37. 1 = 0.043 (I > 2σ(I)) and wR2 = 0.1306 (all data).
38. Methylene chloride was required to dissolve 1 at high enough concentrations to obtain satisfactory NMR spectra of 2. Compound 2 rapidly decomposes in the presence of methylene chloride at room temperature. It was therefore necessary to keep these solutions of 2 at -78 ̊C as much as possible. The catalytic reactions were carried out at lower concentrations of 1 (see Table 1) and, except for one reaction (Table 1, entry 2), in the absence of methylene chloride.
39. 11 in 1.
40. 4).
41. P-P = 49.8 Hz, 1P).
42. P-P = 40.5 Hz, 1P).
43. Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.: Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134. For the rhodium-BINAP-catalyzed hydrogenation of the corresponding acid, see: Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245.
44. Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.: Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc. 1989, 111, 9134. For the rhodium-BINAP-catalyzed hydrogenation of the corresponding acid, see: Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245.
45. Bergens, S. H.; Bosnich, B. J. Am. Chem. Soc. 1991, 113, 958.
46. Massol, M.; Barrau, J.; Stage, J.; Bouyssiers, B. J. Organomet. Chem. 1974, 80, 47.
47. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.