Trifluoromethylated amino alcohols as chiral ligands for highly enantioselective Reformatsky reaction

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 6161-6163

  Fujiwara, Yasuyuki ^a   Katagiri, Toshimasa ^a   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Chiral ligand; Enantioselective Reformatsky reaction; Trifluoromethylated amino alcohol

Indexed keywords

AMINOALCOHOL; ESTER DERIVATIVE; LIGAND;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; REFORMATSKY REACTION; TEMPERATURE SENSITIVITY;

EID: 0038305107     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01392-3     Document Type: Article

References (28)

1. Reformatsky, A. Ber. 1887, 20, 1210.
2. For reviews, see: (a) Organozinc Reagent; Knochel, P.; Philip, J., Eds.; Oxford University Press: New York, 1999; (b) Fürstner, A. Synthesis 1989, 571.
3. For reviews, see: (a) Organozinc Reagent; Knochel, P.; Philip, J., Eds.; Oxford University Press: New York, 1999; (b) Fürstner, A. Synthesis 1989, 571.
4. Reformatsky reaction of PhCHO using chiral ligand. See: (a) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781; (b) Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans.1 1992, 711; (c) Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875; (d) Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1995, 6, 2641; (e) Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. 1995, 1447; (f) Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Synthesis 1996, 1070; (g) Pini, D.; Uccello-Barretta, G.; Mastantuono, A.; Salvadori, P. Tetrahedron 1997, 53, 6065; (h) Andres, J. M.; Martin, Y.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787; (i) Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 3575; (j) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2000, 56, 1217; (k) Ribeiro, C. M. R.; Santos, E. S.; Jardim, A. H. O.; Maia, M. P.; Silva, F. C.; Moreira, A. P. D.; Ferreira, V. F. Tetrahedron: Asymmetry 2002, 13, 1703.
5. Reformatsky reaction of PhCHO using chiral ligand. See: (a) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781; (b) Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans.1 1992, 711; (c) Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875; (d) Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1995, 6, 2641; (e) Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. 1995, 1447; (f) Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Synthesis 1996, 1070; (g) Pini, D.; Uccello-Barretta, G.; Mastantuono, A.; Salvadori, P. Tetrahedron 1997, 53, 6065; (h) Andres, J. M.; Martin, Y.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787; (i) Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 3575; (j) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2000, 56, 1217; (k) Ribeiro, C. M. R.; Santos, E. S.; Jardim, A. H. O.; Maia, M. P.; Silva, F. C.; Moreira, A. P. D.; Ferreira, V. F. Tetrahedron: Asymmetry 2002, 13, 1703.
6. Reformatsky reaction of PhCHO using chiral ligand. See: (a) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781; (b) Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans.1 1992, 711; (c) Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875; (d) Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1995, 6, 2641; (e) Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. 1995, 1447; (f) Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Synthesis 1996, 1070; (g) Pini, D.; Uccello-Barretta, G.; Mastantuono, A.; Salvadori, P. Tetrahedron 1997, 53, 6065; (h) Andres, J. M.; Martin, Y.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787; (i) Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 3575; (j) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2000, 56, 1217; (k) Ribeiro, C. M. R.; Santos, E. S.; Jardim, A. H. O.; Maia, M. P.; Silva, F. C.; Moreira, A. P. D.; Ferreira, V. F. Tetrahedron: Asymmetry 2002, 13, 1703.
7. Reformatsky reaction of PhCHO using chiral ligand. See: (a) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781; (b) Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans.1 1992, 711; (c) Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875; (d) Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1995, 6, 2641; (e) Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. 1995, 1447; (f) Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Synthesis 1996, 1070; (g) Pini, D.; Uccello-Barretta, G.; Mastantuono, A.; Salvadori, P. Tetrahedron 1997, 53, 6065; (h) Andres, J. M.; Martin, Y.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787; (i) Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 3575; (j) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2000, 56, 1217; (k) Ribeiro, C. M. R.; Santos, E. S.; Jardim, A. H. O.; Maia, M. P.; Silva, F. C.; Moreira, A. P. D.; Ferreira, V. F. Tetrahedron: Asymmetry 2002, 13, 1703.
8. Reformatsky reaction of PhCHO using chiral ligand. See: (a) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781; (b) Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans.1 1992, 711; (c) Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875; (d) Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1995, 6, 2641; (e) Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. 1995, 1447; (f) Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Synthesis 1996, 1070; (g) Pini, D.; Uccello-Barretta, G.; Mastantuono, A.; Salvadori, P. Tetrahedron 1997, 53, 6065; (h) Andres, J. M.; Martin, Y.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787; (i) Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 3575; (j) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2000, 56, 1217; (k) Ribeiro, C. M. R.; Santos, E. S.; Jardim, A. H. O.; Maia, M. P.; Silva, F. C.; Moreira, A. P. D.; Ferreira, V. F. Tetrahedron: Asymmetry 2002, 13, 1703.
9. Reformatsky reaction of PhCHO using chiral ligand. See: (a) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781; (b) Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans.1 1992, 711; (c) Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875; (d) Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1995, 6, 2641; (e) Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. 1995, 1447; (f) Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Synthesis 1996, 1070; (g) Pini, D.; Uccello-Barretta, G.; Mastantuono, A.; Salvadori, P. Tetrahedron 1997, 53, 6065; (h) Andres, J. M.; Martin, Y.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787; (i) Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 3575; (j) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2000, 56, 1217; (k) Ribeiro, C. M. R.; Santos, E. S.; Jardim, A. H. O.; Maia, M. P.; Silva, F. C.; Moreira, A. P. D.; Ferreira, V. F. Tetrahedron: Asymmetry 2002, 13, 1703.
10. Reformatsky reaction of PhCHO using chiral ligand. See: (a) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781; (b) Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans.1 1992, 711; (c) Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875; (d) Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1995, 6, 2641; (e) Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. 1995, 1447; (f) Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Synthesis 1996, 1070; (g) Pini, D.; Uccello-Barretta, G.; Mastantuono, A.; Salvadori, P. Tetrahedron 1997, 53, 6065; (h) Andres, J. M.; Martin, Y.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787; (i) Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 3575; (j) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2000, 56, 1217; (k) Ribeiro, C. M. R.; Santos, E. S.; Jardim, A. H. O.; Maia, M. P.; Silva, F. C.; Moreira, A. P. D.; Ferreira, V. F. Tetrahedron: Asymmetry 2002, 13, 1703.
11. Reformatsky reaction of PhCHO using chiral ligand. See: (a) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781; (b) Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans.1 1992, 711; (c) Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875; (d) Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1995, 6, 2641; (e) Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. 1995, 1447; (f) Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Synthesis 1996, 1070; (g) Pini, D.; Uccello-Barretta, G.; Mastantuono, A.; Salvadori, P. Tetrahedron 1997, 53, 6065; (h) Andres, J. M.; Martin, Y.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787; (i) Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 3575; (j) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2000, 56, 1217; (k) Ribeiro, C. M. R.; Santos, E. S.; Jardim, A. H. O.; Maia, M. P.; Silva, F. C.; Moreira, A. P. D.; Ferreira, V. F. Tetrahedron: Asymmetry 2002, 13, 1703.
12. Reformatsky reaction of PhCHO using chiral ligand. See: (a) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781; (b) Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans.1 1992, 711; (c) Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875; (d) Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1995, 6, 2641; (e) Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. 1995, 1447; (f) Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Synthesis 1996, 1070; (g) Pini, D.; Uccello-Barretta, G.; Mastantuono, A.; Salvadori, P. Tetrahedron 1997, 53, 6065; (h) Andres, J. M.; Martin, Y.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787; (i) Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 3575; (j) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2000, 56, 1217; (k) Ribeiro, C. M. R.; Santos, E. S.; Jardim, A. H. O.; Maia, M. P.; Silva, F. C.; Moreira, A. P. D.; Ferreira, V. F. Tetrahedron: Asymmetry 2002, 13, 1703.
13. Reformatsky reaction of PhCHO using chiral ligand. See: (a) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781; (b) Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans.1 1992, 711; (c) Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875; (d) Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1995, 6, 2641; (e) Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. 1995, 1447; (f) Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Synthesis 1996, 1070; (g) Pini, D.; Uccello-Barretta, G.; Mastantuono, A.; Salvadori, P. Tetrahedron 1997, 53, 6065; (h) Andres, J. M.; Martin, Y.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787; (i) Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 3575; (j) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2000, 56, 1217; (k) Ribeiro, C. M. R.; Santos, E. S.; Jardim, A. H. O.; Maia, M. P.; Silva, F. C.; Moreira, A. P. D.; Ferreira, V. F. Tetrahedron: Asymmetry 2002, 13, 1703.
14. Reformatsky reaction of PhCHO using chiral ligand. See: (a) Soai, K.; Kawase, Y. Tetrahedron: Asymmetry 1991, 2, 781; (b) Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc., Perkin Trans.1 1992, 711; (c) Pini, D.; Mastantuono, A.; Salvadori, P. Tetrahedron: Asymmetry 1994, 5, 1875; (d) Mi, A.; Wang, Z.; Chen, Z.; Jiang, Y.; Chan, A. S. C.; Yang, T.-K. Tetrahedron: Asymmetry 1995, 6, 2641; (e) Braun, M.; Vonderhagen, A.; Waldmüller, D. Liebigs Ann. 1995, 1447; (f) Andres, J. M.; Martinez, M. A.; Pedrosa, R.; Perez-Encabo, A. Synthesis 1996, 1070; (g) Pini, D.; Uccello-Barretta, G.; Mastantuono, A.; Salvadori, P. Tetrahedron 1997, 53, 6065; (h) Andres, J. M.; Martin, Y.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 1997, 53, 3787; (i) Zhang, Y.; Wu, W. Tetrahedron: Asymmetry 1997, 8, 3575; (j) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2000, 56, 1217; (k) Ribeiro, C. M. R.; Santos, E. S.; Jardim, A. H. O.; Maia, M. P.; Silva, F. C.; Moreira, A. P. D.; Ferreira, V. F. Tetrahedron: Asymmetry 2002, 13, 1703.
15. Utilization of a special substrate, such as a ketone with chelation effect or imine with a hydroxyl group, was found effective for the asymmetric Reformatsky reactions with better ee's, see: (a) Ojida, A.; Yamano, T.; Taya, N.; Tasaka, A. Org. Lett. 2002, 4, 3051; (b) Ukaji, Y.; Takenaka, S.; Horita, Y.; Inomata, K. Chem. Lett. 2001, 254; (c) Ukaji, Y.; Yoshida, Y.; Inomata, K. Tetrahedron: Asymmetry 2000, 11, 733.
16. Utilization of a special substrate, such as a ketone with chelation effect or imine with a hydroxyl group, was found effective for the asymmetric Reformatsky reactions with better ee's, see: (a) Ojida, A.; Yamano, T.; Taya, N.; Tasaka, A. Org. Lett. 2002, 4, 3051; (b) Ukaji, Y.; Takenaka, S.; Horita, Y.; Inomata, K. Chem. Lett. 2001, 254; (c) Ukaji, Y.; Yoshida, Y.; Inomata, K. Tetrahedron: Asymmetry 2000, 11, 733.
17. Utilization of a special substrate, such as a ketone with chelation effect or imine with a hydroxyl group, was found effective for the asymmetric Reformatsky reactions with better ee's, see: (a) Ojida, A.; Yamano, T.; Taya, N.; Tasaka, A. Org. Lett. 2002, 4, 3051; (b) Ukaji, Y.; Takenaka, S.; Horita, Y.; Inomata, K. Chem. Lett. 2001, 254; (c) Ukaji, Y.; Yoshida, Y.; Inomata, K. Tetrahedron: Asymmetry 2000, 11, 733.
18. Diastereoselective Reformatsky reactions using halo esters with chiral auxiliary or using chiral substrates, see: (a) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2001, 57, 8521; (b) Fukuzawa, S.; Matsuzawa, H.; Yoshimitsu, S. J. Org. Chem. 2000, 65, 1702; (c) Marcotte, S.; Pannecoucke, X.; Feasson, C.; Quirion, J.-C. J. Org. Chem. 1999, 64, 8461; (d) Kagoshima, H.; Hashimoto, Y.; Oguro, D.; Saigo, K. J. Org. Chem. 1998, 63, 691; (e) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 1363; (f) Shankar, B. B.; Kirkup, M. P.; McCombie, S. W.; Clader, J. W.; Ganguly, A. K. Tetrahedron Lett. 1996, 37, 4095.
19. Diastereoselective Reformatsky reactions using halo esters with chiral auxiliary or using chiral substrates, see: (a) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2001, 57, 8521; (b) Fukuzawa, S.; Matsuzawa, H.; Yoshimitsu, S. J. Org. Chem. 2000, 65, 1702; (c) Marcotte, S.; Pannecoucke, X.; Feasson, C.; Quirion, J.-C. J. Org. Chem. 1999, 64, 8461; (d) Kagoshima, H.; Hashimoto, Y.; Oguro, D.; Saigo, K. J. Org. Chem. 1998, 63, 691; (e) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 1363; (f) Shankar, B. B.; Kirkup, M. P.; McCombie, S. W.; Clader, J. W.; Ganguly, A. K. Tetrahedron Lett. 1996, 37, 4095.
20. Diastereoselective Reformatsky reactions using halo esters with chiral auxiliary or using chiral substrates, see: (a) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2001, 57, 8521; (b) Fukuzawa, S.; Matsuzawa, H.; Yoshimitsu, S. J. Org. Chem. 2000, 65, 1702; (c) Marcotte, S.; Pannecoucke, X.; Feasson, C.; Quirion, J.-C. J. Org. Chem. 1999, 64, 8461; (d) Kagoshima, H.; Hashimoto, Y.; Oguro, D.; Saigo, K. J. Org. Chem. 1998, 63, 691; (e) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 1363; (f) Shankar, B. B.; Kirkup, M. P.; McCombie, S. W.; Clader, J. W.; Ganguly, A. K. Tetrahedron Lett. 1996, 37, 4095.
21. Diastereoselective Reformatsky reactions using halo esters with chiral auxiliary or using chiral substrates, see: (a) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2001, 57, 8521; (b) Fukuzawa, S.; Matsuzawa, H.; Yoshimitsu, S. J. Org. Chem. 2000, 65, 1702; (c) Marcotte, S.; Pannecoucke, X.; Feasson, C.; Quirion, J.-C. J. Org. Chem. 1999, 64, 8461; (d) Kagoshima, H.; Hashimoto, Y.; Oguro, D.; Saigo, K. J. Org. Chem. 1998, 63, 691; (e) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 1363; (f) Shankar, B. B.; Kirkup, M. P.; McCombie, S. W.; Clader, J. W.; Ganguly, A. K. Tetrahedron Lett. 1996, 37, 4095.
22. Diastereoselective Reformatsky reactions using halo esters with chiral auxiliary or using chiral substrates, see: (a) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2001, 57, 8521; (b) Fukuzawa, S.; Matsuzawa, H.; Yoshimitsu, S. J. Org. Chem. 2000, 65, 1702; (c) Marcotte, S.; Pannecoucke, X.; Feasson, C.; Quirion, J.-C. J. Org. Chem. 1999, 64, 8461; (d) Kagoshima, H.; Hashimoto, Y.; Oguro, D.; Saigo, K. J. Org. Chem. 1998, 63, 691; (e) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 1363; (f) Shankar, B. B.; Kirkup, M. P.; McCombie, S. W.; Clader, J. W.; Ganguly, A. K. Tetrahedron Lett. 1996, 37, 4095.
23. Diastereoselective Reformatsky reactions using halo esters with chiral auxiliary or using chiral substrates, see: (a) Andres, J. M.; Pedrosa, R.; Perez-Encabo, A. Tetrahedron 2001, 57, 8521; (b) Fukuzawa, S.; Matsuzawa, H.; Yoshimitsu, S. J. Org. Chem. 2000, 65, 1702; (c) Marcotte, S.; Pannecoucke, X.; Feasson, C.; Quirion, J.-C. J. Org. Chem. 1999, 64, 8461; (d) Kagoshima, H.; Hashimoto, Y.; Oguro, D.; Saigo, K. J. Org. Chem. 1998, 63, 691; (e) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 1363; (f) Shankar, B. B.; Kirkup, M. P.; McCombie, S. W.; Clader, J. W.; Ganguly, A. K. Tetrahedron Lett. 1996, 37, 4095.
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27. Preparation and purification of the chiral fluorinated amino alcohols were reported in previous reports, see: (a) Katagiri, T.; Takahashi, M.; Fujiwara, Y.; Ihara, H.; Uneyama, K. J. Org. Chem. 1999, 64, 7323; (b) Katagiri, T.; Ihara, H.; Takahashi, M.; Kashino, S.; Furuhashi, K.; Uneyama, K. Tetrahedron: Asymmetry 1997, 8, 2933.
28. Preparation and purification of the chiral fluorinated amino alcohols were reported in previous reports, see: (a) Katagiri, T.; Takahashi, M.; Fujiwara, Y.; Ihara, H.; Uneyama, K. J. Org. Chem. 1999, 64, 7323; (b) Katagiri, T.; Ihara, H.; Takahashi, M.; Kashino, S.; Furuhashi, K.; Uneyama, K. Tetrahedron: Asymmetry 1997, 8, 2933.