Highly compatible metal and enzyme catalysts for efficient dynamic kinetic resolution of alcohols at ambient temperature

Angewandte Chemie - International Edition

Volumn 43, Issue 47, 2004, Pages 6535-6539

  Martín Matute, Belén ^a   Edin, Michaela ^a   Bogár, Krisztián ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Enantioselectivity; Enzyme catalysis; Kinetic resolution; Reaction mechanisms; Ruthenium

Indexed keywords

ALCOHOLS; ENZYMES; RUTHENIUM; SYNTHESIS (CHEMICAL); TEMPERATURE CONTROL;

ACETATES; ENANTIOSELECTIVE SYNTHESIS; RUTHENIUM CATALYST;

CATALYSIS;

ACETIC ACID DERIVATIVE; ALCOHOL; RUTHENIUM; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYST; ENANTIOSELECTIVITY; ENVIRONMENTAL TEMPERATURE; KINETICS; ROOM TEMPERATURE; SYNTHESIS;

ALCOHOLS; CATALYSIS; KINETICS; LIPASE; METALS; MOLECULAR STRUCTURE; TEMPERATURE;

EID: 11144319821     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461416     Document Type: Article

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40. 3. After 6 min the alcohol was added and the mixture was stirred for 4 min. Finally, isopropenyl acetate was added.
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46. NMR data can be found in the following references: 5a: D. Bianchi, P. Cesti, E. Battistel, J. Org. Chem. 1988, 53, 5531-5535; 5b: J. Y. Legros, M. Toffano, J.-C. Fiaud, Tetrahedron 1995, 51, 3235-3246; 5c: B. R. Rao, M. E. N. Nambudiry, Synth. Commun. 1991, 21, 1721-1727; 5d: S. M. Brown, S. G. Davies, J. A. A. de Sousa, Tetrahedron: Asymmetry 1993, 4, 813-822; 5e: Y. Kita, Y. Takebe, K. Murata, T. Naka, S. Akai, J. Org. Chem. 2000, 65, 83-88; 5f: A. Kamal, M. Sandbhor, K. V. Ramana, Tetrahedron: Asymmetry 2002, 13, 815-820; 5h: reference [5b]; 7: J. S. Wallace, B. W. Baldwin, C. J. Morrow, J. Org. Chem. 1992, 57, 5231-5239.
47. NMR data can be found in the following references: 5a: D. Bianchi, P. Cesti, E. Battistel, J. Org. Chem. 1988, 53, 5531-5535; 5b: J. Y. Legros, M. Toffano, J.-C. Fiaud, Tetrahedron 1995, 51, 3235-3246; 5c: B. R. Rao, M. E. N. Nambudiry, Synth. Commun. 1991, 21, 1721-1727; 5d: S. M. Brown, S. G. Davies, J. A. A. de Sousa, Tetrahedron: Asymmetry 1993, 4, 813-822; 5e: Y. Kita, Y. Takebe, K. Murata, T. Naka, S. Akai, J. Org. Chem. 2000, 65, 83-88; 5f: A. Kamal, M. Sandbhor, K. V. Ramana, Tetrahedron: Asymmetry 2002, 13, 815-820; 5h: reference [5b]; 7: J. S. Wallace, B. W. Baldwin, C. J. Morrow, J. Org. Chem. 1992, 57, 5231-5239.
48. NMR data can be found in the following references: 5a: D. Bianchi, P. Cesti, E. Battistel, J. Org. Chem. 1988, 53, 5531-5535; 5b: J. Y. Legros, M. Toffano, J.-C. Fiaud, Tetrahedron 1995, 51, 3235-3246; 5c: B. R. Rao, M. E. N. Nambudiry, Synth. Commun. 1991, 21, 1721-1727; 5d: S. M. Brown, S. G. Davies, J. A. A. de Sousa, Tetrahedron: Asymmetry 1993, 4, 813-822; 5e: Y. Kita, Y. Takebe, K. Murata, T. Naka, S. Akai, J. Org. Chem. 2000, 65, 83-88; 5f: A. Kamal, M. Sandbhor, K. V. Ramana, Tetrahedron: Asymmetry 2002, 13, 815-820; 5h: reference [5b]; 7: J. S. Wallace, B. W. Baldwin, C. J. Morrow, J. Org. Chem. 1992, 57, 5231-5239.
49. NMR data can be found in the following references: 5a: D. Bianchi, P. Cesti, E. Battistel, J. Org. Chem. 1988, 53, 5531-5535; 5b: J. Y. Legros, M. Toffano, J.-C. Fiaud, Tetrahedron 1995, 51, 3235-3246; 5c: B. R. Rao, M. E. N. Nambudiry, Synth. Commun. 1991, 21, 1721-1727; 5d: S. M. Brown, S. G. Davies, J. A. A. de Sousa, Tetrahedron: Asymmetry 1993, 4, 813-822; 5e: Y. Kita, Y. Takebe, K. Murata, T. Naka, S. Akai, J. Org. Chem. 2000, 65, 83-88; 5f: A. Kamal, M. Sandbhor, K. V. Ramana, Tetrahedron: Asymmetry 2002, 13, 815-820; 5h: reference [5b]; 7: J. S. Wallace, B. W. Baldwin, C. J. Morrow, J. Org. Chem. 1992, 57, 5231-5239.
50. NMR data can be found in the following references: 5a: D. Bianchi, P. Cesti, E. Battistel, J. Org. Chem. 1988, 53, 5531-5535; 5b: J. Y. Legros, M. Toffano, J.-C. Fiaud, Tetrahedron 1995, 51, 3235-3246; 5c: B. R. Rao, M. E. N. Nambudiry, Synth. Commun. 1991, 21, 1721-1727; 5d: S. M. Brown, S. G. Davies, J. A. A. de Sousa, Tetrahedron: Asymmetry 1993, 4, 813-822; 5e: Y. Kita, Y. Takebe, K. Murata, T. Naka, S. Akai, J. Org. Chem. 2000, 65, 83-88; 5f: A. Kamal, M. Sandbhor, K. V. Ramana, Tetrahedron: Asymmetry 2002, 13, 815-820; 5h: reference [5b]; 7: J. S. Wallace, B. W. Baldwin, C. J. Morrow, J. Org. Chem. 1992, 57, 5231-5239.
51. NMR data can be found in the following references: 5a: D. Bianchi, P. Cesti, E. Battistel, J. Org. Chem. 1988, 53, 5531-5535; 5b: J. Y. Legros, M. Toffano, J.-C. Fiaud, Tetrahedron 1995, 51, 3235-3246; 5c: B. R. Rao, M. E. N. Nambudiry, Synth. Commun. 1991, 21, 1721-1727; 5d: S. M. Brown, S. G. Davies, J. A. A. de Sousa, Tetrahedron: Asymmetry 1993, 4, 813-822; 5e: Y. Kita, Y. Takebe, K. Murata, T. Naka, S. Akai, J. Org. Chem. 2000, 65, 83-88; 5f: A. Kamal, M. Sandbhor, K. V. Ramana, Tetrahedron: Asymmetry 2002, 13, 815-820; 5h: reference [5b]; 7: J. S. Wallace, B. W. Baldwin, C. J. Morrow, J. Org. Chem. 1992, 57, 5231-5239.
52. NMR data can be found in the following references: 5a: D. Bianchi, P. Cesti, E. Battistel, J. Org. Chem. 1988, 53, 5531-5535; 5b: J. Y. Legros, M. Toffano, J.-C. Fiaud, Tetrahedron 1995, 51, 3235-3246; 5c: B. R. Rao, M. E. N. Nambudiry, Synth. Commun. 1991, 21, 1721-1727; 5d: S. M. Brown, S. G. Davies, J. A. A. de Sousa, Tetrahedron: Asymmetry 1993, 4, 813-822; 5e: Y. Kita, Y. Takebe, K. Murata, T. Naka, S. Akai, J. Org. Chem. 2000, 65, 83-88; 5f: A. Kamal, M. Sandbhor, K. V. Ramana, Tetrahedron: Asymmetry 2002, 13, 815-820; 5h: reference [5b]; 7: J. S. Wallace, B. W. Baldwin, C. J. Morrow, J. Org. Chem. 1992, 57, 5231-5239.
53. Stirring for 10 min gave essentially the same result but stirring for 1.5 h gave less-reproducible results.