Molecular modeling of salt (lithium chloride) effects on the enantioselectivity of diethylzinc addition to benzaldehyde in the presence of chiral β-amino alcohols

Journal of Organic Chemistry

Volumn 68, Issue 6, 2003, Pages 2369-2375

  Sosa Rivadeneyra, Martha ^a   Muñoz Muñiz, Omar ^b   Anaya de Parrodi, Cecilia ^c   Quintero, Leticia ^a   Juaristi, Eusebio ^b  

^a BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^b DEPARTAMENTO DE FÍSICA   (Mexico)

^c UNIVERSIDAD DE LAS AMÉRICAS PUEBLA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALCOHOLS; ALDEHYDES; CATALYSIS; DERIVATIVES; SUBSTITUTION REACTIONS;

MOLECULAR MODELING;

LITHIUM COMPOUNDS;

AMINOALCOHOL; BENZALDEHYDE; DIETHYLZINC; LITHIUM CHLORIDE; SODIUM CHLORIDE;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; COMPLEX FORMATION; DERIVATIZATION; ENANTIOSELECTIVITY; LIGAND BINDING; MOLECULAR MODEL;

EID: 0345698606     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026811y     Document Type: Article

References (66)

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9. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
10. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
11. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
12. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
13. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
14. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
15. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
16. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
17. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
18. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
19. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
20. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
21. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
22. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
23. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
24. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
25. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
26. For original reports on some of the most successful chiral β-amino alcohol ligands, see: (a) Kitamura, M.; Suga, S.; Kawai, K.; Noyori, R. J. Am. Chem. Soc. 1986, 108, 6071. (b) Tanaka, K.; Ushio, H.; Suzuki, H. J. Chem. Soc., Chem. Commun. 1989, 1700. (c) Nakano, H.; Kumagai, N.; Kabuto, C.; Matsuzaki, H.; Hongo, H. Tetrahedron: Asymmetry 1995, 6, 1233. (d) Soai, K.; Ookawa, A.; Ogawa, K.; Kaba, K. J. Chem. Soc., Chem. Commun. 1987, 467. (e) Urabe, T.; Ushio, H.; Sato, F. Tetrahedron: Asymmetry 1992, 3, 5. (f) Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Oguni, N.; Hayashi, M.; Kaneko, T.; Matsuda Y. J. Organomet. Chem. 1990, 382, 19. (g) Corey, E. J.; Hannon, F. J. Tetrahedron Lett. 1987, 28, 5233. (h) Chaloner, P. A.; Perea, S. A. R. Tetrahedron Lett. 1987, 28, 3013. (i) Hanyu, N.; Aoki, T.; Mino, T.; Sakamoto, M.; Fujita, T. Tetrahedron: Asymmetry 2000, 11, 4127. (j) Dangel, B. D.; Polt, R. Org. Lett. 2000, 2, 3003. (k) Bolm, C.; Zenhnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205. (l) Chrisman, W.; Camara, J. N.; Marcellini, K.; Singaram, B. Goralski, C. T.; Hasha, D. L.; Rudolf, P. R.; Nicholson, L. W.; Borodychuck, K. K. Tetrahedron Lett. 2001, 42, 5805. (m) Pinho, P.; Anderson, P. G. Tetrahedron 2001, 57, 1615. (n) Coob, A. J. A.; Marson, C. M. Tetrahedron: Asymmetry 2001, 12, 1547. (o) Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970. (p) Juanes, O.; Rodríguez-Ubis, J. C.; Brunet, E.; Pennemann, H.; Kossenjans, M.; Martens, J. Eur. J. Org. Chem. 1999, 3323. (q) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361. (r) Wolf, C.; Francis, C. J.; Hawes, P. A.; Shah, M. Tetrahedron: Asymmetry 2002, 13, 1733. (s) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367.
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