Enantiomerically pure N-aryl-β-amino alcohols by enzymatic resolution

Tetrahedron Asymmetry

Volumn 10, Issue 19, 1999, Pages 3663-3666

  Sekar, Govindasamy ^a   Kamble, Rajesh M ^a   Singh, Vinod K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL;

ACETYLATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; ENZYME MECHANISM; HYDROLYSIS; PRIORITY JOURNAL; THIN LAYER CHROMATOGRAPHY;

EID: 0033435118     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00401-2     Document Type: Article

References (28)

1. For general application, see reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (b) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; John Wiley: 1994. (c) Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis; John Wiley & Sons: New York, 1987.
2. For general application, see reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (b) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; John Wiley: 1994. (c) Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis; John Wiley & Sons: New York, 1987.
3. For general application, see reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993. (b) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; John Wiley: 1994. (c) Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis; John Wiley & Sons: New York, 1987.
4. For synthesis of diamines from β-amino alcohols, see: (a) Kokotos, G.; Markidis, T.; Constantinou-Kokotou, V. Synthesis 1996, 1223. (b) Dieter, R. K.; Deo, N.; Lagu, B.; Dieter, J. W. J. Org. Chem. 1992, 57, 1663. (c) Miao, G.; Rossiter, B. E. J. Org. Chem. 1995, 60, 8424. (d) de Sousa, S. E.; O'Brien, P.; Poumellec, P. J. Chem. Soc., Perkin Trans. 1 1998, 1483. (e) Saravanan, P.; Singh, V. K. Tetrahedron Lett. 1998, 39, 167.
5. For synthesis of diamines from β-amino alcohols, see: (a) Kokotos, G.; Markidis, T.; Constantinou-Kokotou, V. Synthesis 1996, 1223. (b) Dieter, R. K.; Deo, N.; Lagu, B.; Dieter, J. W. J. Org. Chem. 1992, 57, 1663. (c) Miao, G.; Rossiter, B. E. J. Org. Chem. 1995, 60, 8424. (d) de Sousa, S. E.; O'Brien, P.; Poumellec, P. J. Chem. Soc., Perkin Trans. 1 1998, 1483. (e) Saravanan, P.; Singh, V. K. Tetrahedron Lett. 1998, 39, 167.
6. For synthesis of diamines from β-amino alcohols, see: (a) Kokotos, G.; Markidis, T.; Constantinou-Kokotou, V. Synthesis 1996, 1223. (b) Dieter, R. K.; Deo, N.; Lagu, B.; Dieter, J. W. J. Org. Chem. 1992, 57, 1663. (c) Miao, G.; Rossiter, B. E. J. Org. Chem. 1995, 60, 8424. (d) de Sousa, S. E.; O'Brien, P.; Poumellec, P. J. Chem. Soc., Perkin Trans. 1 1998, 1483. (e) Saravanan, P.; Singh, V. K. Tetrahedron Lett. 1998, 39, 167.
7. For synthesis of diamines from β-amino alcohols, see: (a) Kokotos, G.; Markidis, T.; Constantinou-Kokotou, V. Synthesis 1996, 1223. (b) Dieter, R. K.; Deo, N.; Lagu, B.; Dieter, J. W. J. Org. Chem. 1992, 57, 1663. (c) Miao, G.; Rossiter, B. E. J. Org. Chem. 1995, 60, 8424. (d) de Sousa, S. E.; O'Brien, P.; Poumellec, P. J. Chem. Soc., Perkin Trans. 1 1998, 1483. (e) Saravanan, P.; Singh, V. K. Tetrahedron Lett. 1998, 39, 167.
8. For synthesis of diamines from β-amino alcohols, see: (a) Kokotos, G.; Markidis, T.; Constantinou-Kokotou, V. Synthesis 1996, 1223. (b) Dieter, R. K.; Deo, N.; Lagu, B.; Dieter, J. W. J. Org. Chem. 1992, 57, 1663. (c) Miao, G.; Rossiter, B. E. J. Org. Chem. 1995, 60, 8424. (d) de Sousa, S. E.; O'Brien, P.; Poumellec, P. J. Chem. Soc., Perkin Trans. 1 1998, 1483. (e) Saravanan, P.; Singh, V. K. Tetrahedron Lett. 1998, 39, 167.
9. For resolution of racemic mixtures, see: (a) Kawai, M.; Omori, Y.; Yamamura, H.; Butsugan, Y. Tetrahedron: Asymmetry 1992, 3, 1019. (b) Sawayama, T.; Tsukamoto, M.; Sasagawa, T.; Naruto, S.; Matsumoto, J.; Uno, H. Chem. Pharm. Bull. 1989, 37, 1382.
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11. For a recent paper on the application of chiral β-amino alcohols in enantioselective autoinductive reduction, see: Shibata, T.; Takahashi, T.; Konishi, T.; Soai, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 2458.
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14. For a recent method for reduction of α-amino acids to β-amino alcohols, see: McKennon, M. J.; Meyers, A. I.; Drauz, K.; Schwarm, M. J. Org. Chem. 1993, 58, 3568.
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20. For some recent references on the use of crude PLE enzyme in the enzymatic hydrolysis of acetates, see: (a) Basavaiah, D.; Krishna, P. R.; Bharathi, T. K. Tetrahedron: Asymmetry 1995, 6, 439, and pertinent references cited therein. (b) Vankar, Y. D.; Kumaravel, G.; Bhattacharya, I.; Vankar, P. S.; Kaur, K. Tetrahedron 1995, 51, 4829. (c) Yadav, V. K.; Kapoor, K. K. Ind. J. Chem. 1995, 34B, 1026. (d) Whitesell, J. K.; Lawrence, R. M. Chimia 1986, 40, 318.
21. For some recent references on the use of crude PLE enzyme in the enzymatic hydrolysis of acetates, see: (a) Basavaiah, D.; Krishna, P. R.; Bharathi, T. K. Tetrahedron: Asymmetry 1995, 6, 439, and pertinent references cited therein. (b) Vankar, Y. D.; Kumaravel, G.; Bhattacharya, I.; Vankar, P. S.; Kaur, K. Tetrahedron 1995, 51, 4829. (c) Yadav, V. K.; Kapoor, K. K. Ind. J. Chem. 1995, 34B, 1026. (d) Whitesell, J. K.; Lawrence, R. M. Chimia 1986, 40, 318.
22. For some recent references on the use of crude PLE enzyme in the enzymatic hydrolysis of acetates, see: (a) Basavaiah, D.; Krishna, P. R.; Bharathi, T. K. Tetrahedron: Asymmetry 1995, 6, 439, and pertinent references cited therein. (b) Vankar, Y. D.; Kumaravel, G.; Bhattacharya, I.; Vankar, P. S.; Kaur, K. Tetrahedron 1995, 51, 4829. (c) Yadav, V. K.; Kapoor, K. K. Ind. J. Chem. 1995, 34B, 1026. (d) Whitesell, J. K.; Lawrence, R. M. Chimia 1986, 40, 318.
23. For some recent references on the use of crude PLE enzyme in the enzymatic hydrolysis of acetates, see: (a) Basavaiah, D.; Krishna, P. R.; Bharathi, T. K. Tetrahedron: Asymmetry 1995, 6, 439, and pertinent references cited therein. (b) Vankar, Y. D.; Kumaravel, G.; Bhattacharya, I.; Vankar, P. S.; Kaur, K. Tetrahedron 1995, 51, 4829. (c) Yadav, V. K.; Kapoor, K. K. Ind. J. Chem. 1995, 34B, 1026. (d) Whitesell, J. K.; Lawrence, R. M. Chimia 1986, 40, 318.
24. The literature search indicated only one Japanese patent where other enzymes have been used to resolve some amino acetates. For reference, see: Application, JP 95-287543 951106; Chem. Abstr. 1997, 127, 80244m.
25. Crude PLE enzyme was prepared according to the literature procedure. For reference, see: Adachi, K.; Kobayashi, S.; Ohno, M. Chimia 1986, 40, 311.
26. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
27. For the effect of organic co-solvent in the PLE enzyme hydrolyzed reactions, see: Guanti, G.; Banfi, L.; Narisano, E.; Riva, R.; Thea, S. Tetrahedron Lett. 1986, 27, 4639.
28. Toone, E. J.; Werth, M. J.; Jones, J. B. J. Am. Chem. Soc. 1990, 112, 4946.