Asymmetric transfer hydrogenation in water with a supported Noyori-Ikariya catalyst

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3321-3324

  Li, Xiaoguang ^a   Wu, Xiaofeng ^a   Chen, Weiping ^a   Hancock, Fred E ^b   King, Frank ^b   Xiao, Jianliang ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b JOHNSON MATTHEY TECHNOLOGY CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; KETONE DERIVATIVE; MACROGOL; RUTHENIUM; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; HYDROGENATION; ION TRANSPORT; REACTION ANALYSIS;

EID: 4644338463     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0487175     Document Type: Article

References (51)

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5. For recent reviews, see: (a) Blaser, H.-U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal 2003, 345, 103-151, (b) Everaere, K.; Mortreux, A.; Carpentier, J.-F. Adv. Synth. Catal. 2003, 345, 67-77. (c) Saluzzo, C.; Lemaire, M. Adv. Synth. Catal. 2002, 344, 915-928. (d) Fan, Q. H.; Li, Y. M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385-3466. (e) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045-2061. (f) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102.
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16. For some recent examples, see: (a) Hannedouche, J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2004, 126, 986-987. (b) Geldbach, T. J.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 8114-8115. (c) Sterk, D.; Stephan, M. S.; Mohar, B. Tetrahedron Lett. 2004, 45, 535-537. (d) Pasto, M.; Riera, A.; Pericas, M. A. Eur. J. Org. Chem. 2002, 2337-2341. (e) Maj, A. M.; Pietrusiewicz, K. M.; Suisse, I.; Agbossou, F.; Mortreux, A. J. Organomet. Chem. 2001, 626, 157-160. (f) Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010-3017. (g) Mizugaki, T.; Kanayama, Y.; Ebitani, K.; Kaneda, K. J. Org. Chem. 1998, 63, 2378-2381. (h) Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226-5228.
17. For some recent examples, see: (a) Hannedouche, J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2004, 126, 986-987. (b) Geldbach, T. J.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 8114-8115. (c) Sterk, D.; Stephan, M. S.; Mohar, B. Tetrahedron Lett. 2004, 45, 535-537. (d) Pasto, M.; Riera, A.; Pericas, M. A. Eur. J. Org. Chem. 2002, 2337-2341. (e) Maj, A. M.; Pietrusiewicz, K. M.; Suisse, I.; Agbossou, F.; Mortreux, A. J. Organomet. Chem. 2001, 626, 157-160. (f) Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010-3017. (g) Mizugaki, T.; Kanayama, Y.; Ebitani, K.; Kaneda, K. J. Org. Chem. 1998, 63, 2378-2381. (h) Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226-5228.
18. For some recent examples, see: (a) Hannedouche, J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2004, 126, 986-987. (b) Geldbach, T. J.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 8114-8115. (c) Sterk, D.; Stephan, M. S.; Mohar, B. Tetrahedron Lett. 2004, 45, 535-537. (d) Pasto, M.; Riera, A.; Pericas, M. A. Eur. J. Org. Chem. 2002, 2337-2341. (e) Maj, A. M.; Pietrusiewicz, K. M.; Suisse, I.; Agbossou, F.; Mortreux, A. J. Organomet. Chem. 2001, 626, 157-160. (f) Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010-3017. (g) Mizugaki, T.; Kanayama, Y.; Ebitani, K.; Kaneda, K. J. Org. Chem. 1998, 63, 2378-2381. (h) Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226-5228.
19. For some recent examples, see: (a) Hannedouche, J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2004, 126, 986-987. (b) Geldbach, T. J.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 8114-8115. (c) Sterk, D.; Stephan, M. S.; Mohar, B. Tetrahedron Lett. 2004, 45, 535-537. (d) Pasto, M.; Riera, A.; Pericas, M. A. Eur. J. Org. Chem. 2002, 2337-2341. (e) Maj, A. M.; Pietrusiewicz, K. M.; Suisse, I.; Agbossou, F.; Mortreux, A. J. Organomet. Chem. 2001, 626, 157-160. (f) Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010-3017. (g) Mizugaki, T.; Kanayama, Y.; Ebitani, K.; Kaneda, K. J. Org. Chem. 1998, 63, 2378-2381. (h) Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226-5228.
20. For some recent examples, see: (a) Hannedouche, J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2004, 126, 986-987. (b) Geldbach, T. J.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 8114-8115. (c) Sterk, D.; Stephan, M. S.; Mohar, B. Tetrahedron Lett. 2004, 45, 535-537. (d) Pasto, M.; Riera, A.; Pericas, M. A. Eur. J. Org. Chem. 2002, 2337-2341. (e) Maj, A. M.; Pietrusiewicz, K. M.; Suisse, I.; Agbossou, F.; Mortreux, A. J. Organomet. Chem. 2001, 626, 157-160. (f) Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010-3017. (g) Mizugaki, T.; Kanayama, Y.; Ebitani, K.; Kaneda, K. J. Org. Chem. 1998, 63, 2378-2381. (h) Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226-5228.
21. For some recent examples, see: (a) Hannedouche, J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2004, 126, 986-987. (b) Geldbach, T. J.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 8114-8115. (c) Sterk, D.; Stephan, M. S.; Mohar, B. Tetrahedron Lett. 2004, 45, 535-537. (d) Pasto, M.; Riera, A.; Pericas, M. A. Eur. J. Org. Chem. 2002, 2337-2341. (e) Maj, A. M.; Pietrusiewicz, K. M.; Suisse, I.; Agbossou, F.; Mortreux, A. J. Organomet. Chem. 2001, 626, 157-160. (f) Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010-3017. (g) Mizugaki, T.; Kanayama, Y.; Ebitani, K.; Kaneda, K. J. Org. Chem. 1998, 63, 2378-2381. (h) Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226-5228.
22. For some recent examples, see: (a) Hannedouche, J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2004, 126, 986-987. (b) Geldbach, T. J.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 8114-8115. (c) Sterk, D.; Stephan, M. S.; Mohar, B. Tetrahedron Lett. 2004, 45, 535-537. (d) Pasto, M.; Riera, A.; Pericas, M. A. Eur. J. Org. Chem. 2002, 2337-2341. (e) Maj, A. M.; Pietrusiewicz, K. M.; Suisse, I.; Agbossou, F.; Mortreux, A. J. Organomet. Chem. 2001, 626, 157-160. (f) Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010-3017. (g) Mizugaki, T.; Kanayama, Y.; Ebitani, K.; Kaneda, K. J. Org. Chem. 1998, 63, 2378-2381. (h) Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226-5228.
23. For some recent examples, see: (a) Hannedouche, J.; Clarkson, G. J.; Wills, M. J. Am. Chem. Soc. 2004, 126, 986-987. (b) Geldbach, T. J.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 8114-8115. (c) Sterk, D.; Stephan, M. S.; Mohar, B. Tetrahedron Lett. 2004, 45, 535-537. (d) Pasto, M.; Riera, A.; Pericas, M. A. Eur. J. Org. Chem. 2002, 2337-2341. (e) Maj, A. M.; Pietrusiewicz, K. M.; Suisse, I.; Agbossou, F.; Mortreux, A. J. Organomet. Chem. 2001, 626, 157-160. (f) Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010-3017. (g) Mizugaki, T.; Kanayama, Y.; Ebitani, K.; Kaneda, K. J. Org. Chem. 1998, 63, 2378-2381. (h) Palmer, M.; Walsgrove, T.; Wills, M. J. Org. Chem. 1997, 62, 5226-5228.
24. For examples of supported TsDPEN and related diamines, see: (a) Liu, P. N.; Gu, P. M.; Wang, F.; Tu, Y. Q. Org. Lett. 2004, 6, 169-172. (b) Itsuno, S.; Tsuji, A.; Takahashi, M. Tetrahedron Lett. 2003, 44, 3825-3828. (c) Chen, Y.-C.; Wu, T.-F.; Deng, J.-G.; Liu, H.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Chem. Commun. 2001, 1488-1489. (d) Touchard, F.; Fache, F.; Lemaire, M. Eur. J. Org. Chem. 2000, 3787-3792. (e) Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9, 2015-2018. (f) ter Halle, R.; Schulz, E.; Lemaire, M. Synlett 1997, 1257-1258.
25. For examples of supported TsDPEN and related diamines, see: (a) Liu, P. N.; Gu, P. M.; Wang, F.; Tu, Y. Q. Org. Lett. 2004, 6, 169-172. (b) Itsuno, S.; Tsuji, A.; Takahashi, M. Tetrahedron Lett. 2003, 44, 3825-3828. (c) Chen, Y.-C.; Wu, T.-F.; Deng, J.-G.; Liu, H.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Chem. Commun. 2001, 1488-1489. (d) Touchard, F.; Fache, F.; Lemaire, M. Eur. J. Org. Chem. 2000, 3787-3792. (e) Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9, 2015-2018. (f) ter Halle, R.; Schulz, E.; Lemaire, M. Synlett 1997, 1257-1258.
26. For examples of supported TsDPEN and related diamines, see: (a) Liu, P. N.; Gu, P. M.; Wang, F.; Tu, Y. Q. Org. Lett. 2004, 6, 169-172. (b) Itsuno, S.; Tsuji, A.; Takahashi, M. Tetrahedron Lett. 2003, 44, 3825-3828. (c) Chen, Y.-C.; Wu, T.-F.; Deng, J.-G.; Liu, H.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Chem. Commun. 2001, 1488-1489. (d) Touchard, F.; Fache, F.; Lemaire, M. Eur. J. Org. Chem. 2000, 3787-3792. (e) Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9, 2015-2018. (f) ter Halle, R.; Schulz, E.; Lemaire, M. Synlett 1997, 1257-1258.
27. For examples of supported TsDPEN and related diamines, see: (a) Liu, P. N.; Gu, P. M.; Wang, F.; Tu, Y. Q. Org. Lett. 2004, 6, 169-172. (b) Itsuno, S.; Tsuji, A.; Takahashi, M. Tetrahedron Lett. 2003, 44, 3825-3828. (c) Chen, Y.-C.; Wu, T.-F.; Deng, J.-G.; Liu, H.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Chem. Commun. 2001, 1488-1489. (d) Touchard, F.; Fache, F.; Lemaire, M. Eur. J. Org. Chem. 2000, 3787-3792. (e) Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9, 2015-2018. (f) ter Halle, R.; Schulz, E.; Lemaire, M. Synlett 1997, 1257-1258.
28. For examples of supported TsDPEN and related diamines, see: (a) Liu, P. N.; Gu, P. M.; Wang, F.; Tu, Y. Q. Org. Lett. 2004, 6, 169-172. (b) Itsuno, S.; Tsuji, A.; Takahashi, M. Tetrahedron Lett. 2003, 44, 3825-3828. (c) Chen, Y.-C.; Wu, T.-F.; Deng, J.-G.; Liu, H.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Chem. Commun. 2001, 1488-1489. (d) Touchard, F.; Fache, F.; Lemaire, M. Eur. J. Org. Chem. 2000, 3787-3792. (e) Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9, 2015-2018. (f) ter Halle, R.; Schulz, E.; Lemaire, M. Synlett 1997, 1257-1258.
29. For examples of supported TsDPEN and related diamines, see: (a) Liu, P. N.; Gu, P. M.; Wang, F.; Tu, Y. Q. Org. Lett. 2004, 6, 169-172. (b) Itsuno, S.; Tsuji, A.; Takahashi, M. Tetrahedron Lett. 2003, 44, 3825-3828. (c) Chen, Y.-C.; Wu, T.-F.; Deng, J.-G.; Liu, H.; Jiang, Y.-Z.; Choi, M. C. K.; Chan, A. S. C. Chem. Commun. 2001, 1488-1489. (d) Touchard, F.; Fache, F.; Lemaire, M. Eur. J. Org. Chem. 2000, 3787-3792. (e) Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9, 2015-2018. (f) ter Halle, R.; Schulz, E.; Lemaire, M. Synlett 1997, 1257-1258.
30. For literature about aqueous-phase asymmetric transfer hydrogenation of ketones, see: (a) Ma, Y. P.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. G. Org. Lett. 2003, 5, 2103-2106. (b) Himeda, Y.; Onozawa-Komatsuzaki, N.; Sugihara, H.; Arakawa, H.; Kasuga, K. J. Mol. Catal. A: Chem. 2003, 195, 95-100. (c) Rhyoo, H. Y.; Park, H. J.; Suh, W. H.; Chung, Y. K. Tetrahedron Lett. 2002, 43, 269-272. (d) Rhyoo, H. Y.; Park, H. J.; Chung, Y. K. Chem. Commun. 2001, 2064-2065. (e) Thorpe, T.; Blacker, J.; Brown, S. M.; Hubert, C.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4041-4043. (f) Bubert, C.; Blacker, J.; Brown, S. M.; Crosby, J.; Fitsjohn, S.; Muxworthy, J. P.; Thorpe, T.; Williams, J. M. Tetrahedron Lett. 2001, 42, 4037-4039. (g) Ogo, S.; Makihara, N.; and Watanabe, Y. Organometallics 1999, 18, 5470-5474.
31. For literature about aqueous-phase asymmetric transfer hydrogenation of ketones, see: (a) Ma, Y. P.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. G. Org. Lett. 2003, 5, 2103-2106. (b) Himeda, Y.; Onozawa-Komatsuzaki, N.; Sugihara, H.; Arakawa, H.; Kasuga, K. J. Mol. Catal. A: Chem. 2003, 195, 95-100. (c) Rhyoo, H. Y.; Park, H. J.; Suh, W. H.; Chung, Y. K. Tetrahedron Lett. 2002, 43, 269-272. (d) Rhyoo, H. Y.; Park, H. J.; Chung, Y. K. Chem. Commun. 2001, 2064-2065. (e) Thorpe, T.; Blacker, J.; Brown, S. M.; Hubert, C.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4041-4043. (f) Bubert, C.; Blacker, J.; Brown, S. M.; Crosby, J.; Fitsjohn, S.; Muxworthy, J. P.; Thorpe, T.; Williams, J. M. Tetrahedron Lett. 2001, 42, 4037-4039. (g) Ogo, S.; Makihara, N.; and Watanabe, Y. Organometallics 1999, 18, 5470-5474.
32. For literature about aqueous-phase asymmetric transfer hydrogenation of ketones, see: (a) Ma, Y. P.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. G. Org. Lett. 2003, 5, 2103-2106. (b) Himeda, Y.; Onozawa-Komatsuzaki, N.; Sugihara, H.; Arakawa, H.; Kasuga, K. J. Mol. Catal. A: Chem. 2003, 195, 95-100. (c) Rhyoo, H. Y.; Park, H. J.; Suh, W. H.; Chung, Y. K. Tetrahedron Lett. 2002, 43, 269-272. (d) Rhyoo, H. Y.; Park, H. J.; Chung, Y. K. Chem. Commun. 2001, 2064-2065. (e) Thorpe, T.; Blacker, J.; Brown, S. M.; Hubert, C.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4041-4043. (f) Bubert, C.; Blacker, J.; Brown, S. M.; Crosby, J.; Fitsjohn, S.; Muxworthy, J. P.; Thorpe, T.; Williams, J. M. Tetrahedron Lett. 2001, 42, 4037-4039. (g) Ogo, S.; Makihara, N.; and Watanabe, Y. Organometallics 1999, 18, 5470-5474.
33. For literature about aqueous-phase asymmetric transfer hydrogenation of ketones, see: (a) Ma, Y. P.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. G. Org. Lett. 2003, 5, 2103-2106. (b) Himeda, Y.; Onozawa-Komatsuzaki, N.; Sugihara, H.; Arakawa, H.; Kasuga, K. J. Mol. Catal. A: Chem. 2003, 195, 95-100. (c) Rhyoo, H. Y.; Park, H. J.; Suh, W. H.; Chung, Y. K. Tetrahedron Lett. 2002, 43, 269-272. (d) Rhyoo, H. Y.; Park, H. J.; Chung, Y. K. Chem. Commun. 2001, 2064-2065. (e) Thorpe, T.; Blacker, J.; Brown, S. M.; Hubert, C.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4041-4043. (f) Bubert, C.; Blacker, J.; Brown, S. M.; Crosby, J.; Fitsjohn, S.; Muxworthy, J. P.; Thorpe, T.; Williams, J. M. Tetrahedron Lett. 2001, 42, 4037-4039. (g) Ogo, S.; Makihara, N.; and Watanabe, Y. Organometallics 1999, 18, 5470-5474.
34. For literature about aqueous-phase asymmetric transfer hydrogenation of ketones, see: (a) Ma, Y. P.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. G. Org. Lett. 2003, 5, 2103-2106. (b) Himeda, Y.; Onozawa-Komatsuzaki, N.; Sugihara, H.; Arakawa, H.; Kasuga, K. J. Mol. Catal. A: Chem. 2003, 195, 95-100. (c) Rhyoo, H. Y.; Park, H. J.; Suh, W. H.; Chung, Y. K. Tetrahedron Lett. 2002, 43, 269-272. (d) Rhyoo, H. Y.; Park, H. J.; Chung, Y. K. Chem. Commun. 2001, 2064-2065. (e) Thorpe, T.; Blacker, J.; Brown, S. M.; Hubert, C.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4041-4043. (f) Bubert, C.; Blacker, J.; Brown, S. M.; Crosby, J.; Fitsjohn, S.; Muxworthy, J. P.; Thorpe, T.; Williams, J. M. Tetrahedron Lett. 2001, 42, 4037-4039. (g) Ogo, S.; Makihara, N.; and Watanabe, Y. Organometallics 1999, 18, 5470-5474.
35. For literature about aqueous-phase asymmetric transfer hydrogenation of ketones, see: (a) Ma, Y. P.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. G. Org. Lett. 2003, 5, 2103-2106. (b) Himeda, Y.; Onozawa-Komatsuzaki, N.; Sugihara, H.; Arakawa, H.; Kasuga, K. J. Mol. Catal. A: Chem. 2003, 195, 95-100. (c) Rhyoo, H. Y.; Park, H. J.; Suh, W. H.; Chung, Y. K. Tetrahedron Lett. 2002, 43, 269-272. (d) Rhyoo, H. Y.; Park, H. J.; Chung, Y. K. Chem. Commun. 2001, 2064-2065. (e) Thorpe, T.; Blacker, J.; Brown, S. M.; Hubert, C.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4041-4043. (f) Bubert, C.; Blacker, J.; Brown, S. M.; Crosby, J.; Fitsjohn, S.; Muxworthy, J. P.; Thorpe, T.; Williams, J. M. Tetrahedron Lett. 2001, 42, 4037-4039. (g) Ogo, S.; Makihara, N.; and Watanabe, Y. Organometallics 1999, 18, 5470-5474.
36. For literature about aqueous-phase asymmetric transfer hydrogenation of ketones, see: (a) Ma, Y. P.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. G. Org. Lett. 2003, 5, 2103-2106. (b) Himeda, Y.; Onozawa-Komatsuzaki, N.; Sugihara, H.; Arakawa, H.; Kasuga, K. J. Mol. Catal. A: Chem. 2003, 195, 95-100. (c) Rhyoo, H. Y.; Park, H. J.; Suh, W. H.; Chung, Y. K. Tetrahedron Lett. 2002, 43, 269-272. (d) Rhyoo, H. Y.; Park, H. J.; Chung, Y. K. Chem. Commun. 2001, 2064-2065. (e) Thorpe, T.; Blacker, J.; Brown, S. M.; Hubert, C.; Crosby, J.; Fitzjohn, S.; Muxworthy, J. P.; Williams, J. M. J. Tetrahedron Lett. 2001, 42, 4041-4043. (f) Bubert, C.; Blacker, J.; Brown, S. M.; Crosby, J.; Fitsjohn, S.; Muxworthy, J. P.; Thorpe, T.; Williams, J. M. Tetrahedron Lett. 2001, 42, 4037-4039. (g) Ogo, S.; Makihara, N.; and Watanabe, Y. Organometallics 1999, 18, 5470-5474.
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48. For recent mechanistic studies, see: (a) Koike, T.; Ikariya, T. Adv. Synth. Catal. 2004, 346, 37-41. (b) Brandt, P.; Roth, P.; Andersson, P. G. J. Org. Chem. 2004, 69, 4885-4890 and references therein. (c) Casey, C. P.; Johnson, J. B. J. Org. Chem. 2003, 68, 1998-2001. (d) Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931-7944.
49. For recent mechanistic studies, see: (a) Koike, T.; Ikariya, T. Adv. Synth. Catal. 2004, 346, 37-41. (b) Brandt, P.; Roth, P.; Andersson, P. G. J. Org. Chem. 2004, 69, 4885-4890 and references therein. (c) Casey, C. P.; Johnson, J. B. J. Org. Chem. 2003, 68, 1998-2001. (d) Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931-7944.
50. For recent mechanistic studies, see: (a) Koike, T.; Ikariya, T. Adv. Synth. Catal. 2004, 346, 37-41. (b) Brandt, P.; Roth, P.; Andersson, P. G. J. Org. Chem. 2004, 69, 4885-4890 and references therein. (c) Casey, C. P.; Johnson, J. B. J. Org. Chem. 2003, 68, 1998-2001. (d) Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931-7944.
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