Chemo-enzymatic preparation of optically active endo- bicyclo[4.1.0]heptan-2-ols

Tetrahedron Asymmetry

Volumn 10, Issue 6, 1999, Pages 1107-1117

  Barnier, Jean Pierre ^a   Morisson, Véronique ^a   Volle, Isabelle ^a   Blanco, Luis ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; BICYCLO[4.1.0]HEPTAN 2 OL; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ENANTIOMER; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0001003186     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00099-3     Document Type: Article

References (82)

1. trans- and cis-2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hexan-2-ols (sabinene hydrates) are present in many plants. Some bicyclo[4.1.0]heptan-2-ols are also presents in plants, for the 4,7,7-trimethylated compound (caran-5-ol) see: Handilou, E.; Kokkini, S.; Kokkalou, E. Biochem. Syst. Ecol. 1992, 20, 33-40. Handilou, E.; Kokkalou, E.; Kokkini, S. Planta Med. 1992, 58, 105-107. Komaitis, M. E.; Ifanti-Papatragianni, N.; Melissari-Panagiotou, E. Food Chem. 1992, 45, 117-118. Chen, Y.; Li, Z.; Li, H. Chromatographia 1987, 23, 502-506, for the 3,7,7-trimethylated compound (caran-2-ol) see Chen, Y.; Li, X. Linchan Huaxue Yu Gongye 1992, 12, 159-163, for the 2,5-dimethyl-5-(4-methylpent-3-enyl)bicycloheptanol (chenopodanol) see: Tori, M.; Hamaguchi, T.; Aoki, M.; Sono, M.; Asakawa, Y. Can. J. Chem. 1997, 75, 634-640. For another example of a natural compound isolated from a marine mollusc with a 6-oxabicyclo[6.1.0]nonan-2-ol framework see: Miyamoto, T.; Ebisawa, Y.; Higuchi, R. Tetrahedron Lett. 1995, 36, 6073-6074.
2. trans- and cis-2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hexan-2-ols (sabinene hydrates) are present in many plants. Some bicyclo[4.1.0]heptan-2-ols are also presents in plants, for the 4,7,7-trimethylated compound (caran-5-ol) see: Handilou, E.; Kokkini, S.; Kokkalou, E. Biochem. Syst. Ecol. 1992, 20, 33-40. Handilou, E.; Kokkalou, E.; Kokkini, S. Planta Med. 1992, 58, 105-107. Komaitis, M. E.; Ifanti-Papatragianni, N.; Melissari-Panagiotou, E. Food Chem. 1992, 45, 117-118. Chen, Y.; Li, Z.; Li, H. Chromatographia 1987, 23, 502-506, for the 3,7,7-trimethylated compound (caran-2-ol) see Chen, Y.; Li, X. Linchan Huaxue Yu Gongye 1992, 12, 159-163, for the 2,5-dimethyl-5-(4-methylpent-3-enyl)bicycloheptanol (chenopodanol) see: Tori, M.; Hamaguchi, T.; Aoki, M.; Sono, M.; Asakawa, Y. Can. J. Chem. 1997, 75, 634-640. For another example of a natural compound isolated from a marine mollusc with a 6-oxabicyclo[6.1.0]nonan-2-ol framework see: Miyamoto, T.; Ebisawa, Y.; Higuchi, R. Tetrahedron Lett. 1995, 36, 6073-6074.
3. trans- and cis-2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hexan-2-ols (sabinene hydrates) are present in many plants. Some bicyclo[4.1.0]heptan-2-ols are also presents in plants, for the 4,7,7-trimethylated compound (caran-5-ol) see: Handilou, E.; Kokkini, S.; Kokkalou, E. Biochem. Syst. Ecol. 1992, 20, 33-40. Handilou, E.; Kokkalou, E.; Kokkini, S. Planta Med. 1992, 58, 105-107. Komaitis, M. E.; Ifanti-Papatragianni, N.; Melissari-Panagiotou, E. Food Chem. 1992, 45, 117-118. Chen, Y.; Li, Z.; Li, H. Chromatographia 1987, 23, 502-506, for the 3,7,7-trimethylated compound (caran-2-ol) see Chen, Y.; Li, X. Linchan Huaxue Yu Gongye 1992, 12, 159-163, for the 2,5-dimethyl-5-(4-methylpent-3-enyl)bicycloheptanol (chenopodanol) see: Tori, M.; Hamaguchi, T.; Aoki, M.; Sono, M.; Asakawa, Y. Can. J. Chem. 1997, 75, 634-640. For another example of a natural compound isolated from a marine mollusc with a 6-oxabicyclo[6.1.0]nonan-2-ol framework see: Miyamoto, T.; Ebisawa, Y.; Higuchi, R. Tetrahedron Lett. 1995, 36, 6073-6074.
4. trans- and cis-2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hexan-2-ols (sabinene hydrates) are present in many plants. Some bicyclo[4.1.0]heptan-2-ols are also presents in plants, for the 4,7,7-trimethylated compound (caran-5-ol) see: Handilou, E.; Kokkini, S.; Kokkalou, E. Biochem. Syst. Ecol. 1992, 20, 33-40. Handilou, E.; Kokkalou, E.; Kokkini, S. Planta Med. 1992, 58, 105-107. Komaitis, M. E.; Ifanti-Papatragianni, N.; Melissari-Panagiotou, E. Food Chem. 1992, 45, 117-118. Chen, Y.; Li, Z.; Li, H. Chromatographia 1987, 23, 502-506, for the 3,7,7-trimethylated compound (caran-2-ol) see Chen, Y.; Li, X. Linchan Huaxue Yu Gongye 1992, 12, 159-163, for the 2,5-dimethyl-5-(4-methylpent-3-enyl)bicycloheptanol (chenopodanol) see: Tori, M.; Hamaguchi, T.; Aoki, M.; Sono, M.; Asakawa, Y. Can. J. Chem. 1997, 75, 634-640. For another example of a natural compound isolated from a marine mollusc with a 6-oxabicyclo[6.1.0]nonan-2-ol framework see: Miyamoto, T.; Ebisawa, Y.; Higuchi, R. Tetrahedron Lett. 1995, 36, 6073-6074.
5. trans- and cis-2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hexan-2-ols (sabinene hydrates) are present in many plants. Some bicyclo[4.1.0]heptan-2-ols are also presents in plants, for the 4,7,7-trimethylated compound (caran-5-ol) see: Handilou, E.; Kokkini, S.; Kokkalou, E. Biochem. Syst. Ecol. 1992, 20, 33-40. Handilou, E.; Kokkalou, E.; Kokkini, S. Planta Med. 1992, 58, 105-107. Komaitis, M. E.; Ifanti-Papatragianni, N.; Melissari-Panagiotou, E. Food Chem. 1992, 45, 117-118. Chen, Y.; Li, Z.; Li, H. Chromatographia 1987, 23, 502-506, for the 3,7,7-trimethylated compound (caran-2-ol) see Chen, Y.; Li, X. Linchan Huaxue Yu Gongye 1992, 12, 159-163, for the 2,5-dimethyl-5-(4-methylpent-3-enyl)bicycloheptanol (chenopodanol) see: Tori, M.; Hamaguchi, T.; Aoki, M.; Sono, M.; Asakawa, Y. Can. J. Chem. 1997, 75, 634-640. For another example of a natural compound isolated from a marine mollusc with a 6-oxabicyclo[6.1.0]nonan-2-ol framework see: Miyamoto, T.; Ebisawa, Y.; Higuchi, R. Tetrahedron Lett. 1995, 36, 6073-6074.
6. trans- and cis-2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hexan-2-ols (sabinene hydrates) are present in many plants. Some bicyclo[4.1.0]heptan-2-ols are also presents in plants, for the 4,7,7-trimethylated compound (caran-5-ol) see: Handilou, E.; Kokkini, S.; Kokkalou, E. Biochem. Syst. Ecol. 1992, 20, 33-40. Handilou, E.; Kokkalou, E.; Kokkini, S. Planta Med. 1992, 58, 105-107. Komaitis, M. E.; Ifanti-Papatragianni, N.; Melissari-Panagiotou, E. Food Chem. 1992, 45, 117-118. Chen, Y.; Li, Z.; Li, H. Chromatographia 1987, 23, 502-506, for the 3,7,7-trimethylated compound (caran-2-ol) see Chen, Y.; Li, X. Linchan Huaxue Yu Gongye 1992, 12, 159-163, for the 2,5-dimethyl-5-(4-methylpent-3-enyl)bicycloheptanol (chenopodanol) see: Tori, M.; Hamaguchi, T.; Aoki, M.; Sono, M.; Asakawa, Y. Can. J. Chem. 1997, 75, 634-640. For another example of a natural compound isolated from a marine mollusc with a 6-oxabicyclo[6.1.0]nonan-2-ol framework see: Miyamoto, T.; Ebisawa, Y.; Higuchi, R. Tetrahedron Lett. 1995, 36, 6073-6074.
7. trans- and cis-2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hexan-2-ols (sabinene hydrates) are present in many plants. Some bicyclo[4.1.0]heptan-2-ols are also presents in plants, for the 4,7,7-trimethylated compound (caran-5-ol) see: Handilou, E.; Kokkini, S.; Kokkalou, E. Biochem. Syst. Ecol. 1992, 20, 33-40. Handilou, E.; Kokkalou, E.; Kokkini, S. Planta Med. 1992, 58, 105-107. Komaitis, M. E.; Ifanti-Papatragianni, N.; Melissari-Panagiotou, E. Food Chem. 1992, 45, 117-118. Chen, Y.; Li, Z.; Li, H. Chromatographia 1987, 23, 502-506, for the 3,7,7-trimethylated compound (caran-2-ol) see Chen, Y.; Li, X. Linchan Huaxue Yu Gongye 1992, 12, 159-163, for the 2,5-dimethyl-5-(4-methylpent-3-enyl)bicycloheptanol (chenopodanol) see: Tori, M.; Hamaguchi, T.; Aoki, M.; Sono, M.; Asakawa, Y. Can. J. Chem. 1997, 75, 634-640. For another example of a natural compound isolated from a marine mollusc with a 6-oxabicyclo[6.1.0]nonan-2-ol framework see: Miyamoto, T.; Ebisawa, Y.; Higuchi, R. Tetrahedron Lett. 1995, 36, 6073-6074.
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45. For other examples of lipase-catalyzed preparations of optically active cyclopropyl alcohol derivatives see: Csuk, R.; von Scholz, Y. Tetrahedron 1996, 52, 6383-6396. Krief, A.; Surleraux, D.; Ropson, N. Tetrahedron: Asymmetry 1993, 4, 289-292; Theil, F.; Schick, H.; Winter, G.; Reck, G. Tetrahedron 1991, 47, 7569-7582; Theil, F.; Kunath, A.; Schick, H. Tetrahedron Lett. 1992, 33, 3457-3460; Granjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215-1230; Ader, U.; Breitgoff, D.; Klein, P.; Laumen, K. E.; Schneider, M. P. Tetrahedron Lett. 1989, 30, 1793-1796; Laumen, K.; Schneider, M. Tetrahedron Lett. 1985, 26, 2073-2076; Rasel, W.; Hultin, P. G.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1985, 1563-1564; Rogers, D. H.; Yi, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941-945.
46. For other examples of lipase-catalyzed preparations of optically active cyclopropyl alcohol derivatives see: Csuk, R.; von Scholz, Y. Tetrahedron 1996, 52, 6383-6396. Krief, A.; Surleraux, D.; Ropson, N. Tetrahedron: Asymmetry 1993, 4, 289-292; Theil, F.; Schick, H.; Winter, G.; Reck, G. Tetrahedron 1991, 47, 7569-7582; Theil, F.; Kunath, A.; Schick, H. Tetrahedron Lett. 1992, 33, 3457-3460; Granjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215-1230; Ader, U.; Breitgoff, D.; Klein, P.; Laumen, K. E.; Schneider, M. P. Tetrahedron Lett. 1989, 30, 1793-1796; Laumen, K.; Schneider, M. Tetrahedron Lett. 1985, 26, 2073-2076; Rasel, W.; Hultin, P. G.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1985, 1563-1564; Rogers, D. H.; Yi, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941-945.
47. For other examples of lipase-catalyzed preparations of optically active cyclopropyl alcohol derivatives see: Csuk, R.; von Scholz, Y. Tetrahedron 1996, 52, 6383-6396. Krief, A.; Surleraux, D.; Ropson, N. Tetrahedron: Asymmetry 1993, 4, 289-292; Theil, F.; Schick, H.; Winter, G.; Reck, G. Tetrahedron 1991, 47, 7569-7582; Theil, F.; Kunath, A.; Schick, H. Tetrahedron Lett. 1992, 33, 3457-3460; Granjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215-1230; Ader, U.; Breitgoff, D.; Klein, P.; Laumen, K. E.; Schneider, M. P. Tetrahedron Lett. 1989, 30, 1793-1796; Laumen, K.; Schneider, M. Tetrahedron Lett. 1985, 26, 2073-2076; Rasel, W.; Hultin, P. G.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1985, 1563-1564; Rogers, D. H.; Yi, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941-945.
48. For other examples of lipase-catalyzed preparations of optically active cyclopropyl alcohol derivatives see: Csuk, R.; von Scholz, Y. Tetrahedron 1996, 52, 6383-6396. Krief, A.; Surleraux, D.; Ropson, N. Tetrahedron: Asymmetry 1993, 4, 289-292; Theil, F.; Schick, H.; Winter, G.; Reck, G. Tetrahedron 1991, 47, 7569-7582; Theil, F.; Kunath, A.; Schick, H. Tetrahedron Lett. 1992, 33, 3457-3460; Granjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215-1230; Ader, U.; Breitgoff, D.; Klein, P.; Laumen, K. E.; Schneider, M. P. Tetrahedron Lett. 1989, 30, 1793-1796; Laumen, K.; Schneider, M. Tetrahedron Lett. 1985, 26, 2073-2076; Rasel, W.; Hultin, P. G.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1985, 1563-1564; Rogers, D. H.; Yi, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941-945.
49. For other examples of lipase-catalyzed preparations of optically active cyclopropyl alcohol derivatives see: Csuk, R.; von Scholz, Y. Tetrahedron 1996, 52, 6383-6396. Krief, A.; Surleraux, D.; Ropson, N. Tetrahedron: Asymmetry 1993, 4, 289-292; Theil, F.; Schick, H.; Winter, G.; Reck, G. Tetrahedron 1991, 47, 7569-7582; Theil, F.; Kunath, A.; Schick, H. Tetrahedron Lett. 1992, 33, 3457-3460; Granjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215-1230; Ader, U.; Breitgoff, D.; Klein, P.; Laumen, K. E.; Schneider, M. P. Tetrahedron Lett. 1989, 30, 1793-1796; Laumen, K.; Schneider, M. Tetrahedron Lett. 1985, 26, 2073-2076; Rasel, W.; Hultin, P. G.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1985, 1563-1564; Rogers, D. H.; Yi, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941-945.
50. For other examples of lipase-catalyzed preparations of optically active cyclopropyl alcohol derivatives see: Csuk, R.; von Scholz, Y. Tetrahedron 1996, 52, 6383-6396. Krief, A.; Surleraux, D.; Ropson, N. Tetrahedron: Asymmetry 1993, 4, 289-292; Theil, F.; Schick, H.; Winter, G.; Reck, G. Tetrahedron 1991, 47, 7569-7582; Theil, F.; Kunath, A.; Schick, H. Tetrahedron Lett. 1992, 33, 3457-3460; Granjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215-1230; Ader, U.; Breitgoff, D.; Klein, P.; Laumen, K. E.; Schneider, M. P. Tetrahedron Lett. 1989, 30, 1793-1796; Laumen, K.; Schneider, M. Tetrahedron Lett. 1985, 26, 2073-2076; Rasel, W.; Hultin, P. G.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1985, 1563-1564; Rogers, D. H.; Yi, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941-945.
51. For other examples of lipase-catalyzed preparations of optically active cyclopropyl alcohol derivatives see: Csuk, R.; von Scholz, Y. Tetrahedron 1996, 52, 6383-6396. Krief, A.; Surleraux, D.; Ropson, N. Tetrahedron: Asymmetry 1993, 4, 289-292; Theil, F.; Schick, H.; Winter, G.; Reck, G. Tetrahedron 1991, 47, 7569-7582; Theil, F.; Kunath, A.; Schick, H. Tetrahedron Lett. 1992, 33, 3457-3460; Granjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215-1230; Ader, U.; Breitgoff, D.; Klein, P.; Laumen, K. E.; Schneider, M. P. Tetrahedron Lett. 1989, 30, 1793-1796; Laumen, K.; Schneider, M. Tetrahedron Lett. 1985, 26, 2073-2076; Rasel, W.; Hultin, P. G.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1985, 1563-1564; Rogers, D. H.; Yi, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941-945.
52. For other examples of lipase-catalyzed preparations of optically active cyclopropyl alcohol derivatives see: Csuk, R.; von Scholz, Y. Tetrahedron 1996, 52, 6383-6396. Krief, A.; Surleraux, D.; Ropson, N. Tetrahedron: Asymmetry 1993, 4, 289-292; Theil, F.; Schick, H.; Winter, G.; Reck, G. Tetrahedron 1991, 47, 7569-7582; Theil, F.; Kunath, A.; Schick, H. Tetrahedron Lett. 1992, 33, 3457-3460; Granjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215-1230; Ader, U.; Breitgoff, D.; Klein, P.; Laumen, K. E.; Schneider, M. P. Tetrahedron Lett. 1989, 30, 1793-1796; Laumen, K.; Schneider, M. Tetrahedron Lett. 1985, 26, 2073-2076; Rasel, W.; Hultin, P. G.; Jones, J. B. J. Chem. Soc., Chem. Commun. 1985, 1563-1564; Rogers, D. H.; Yi, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941-945.
53. Miyano, S.; Izumi, Y.; Fujii, H.; Hashimoto, H. Synthesis 1977, 700-701.
54. Denmark, S. E.; Edwards, J. P. J. Org. Chem. 1991, 56, 6974-6981. In these reactions the exo diastereoisomers were not noticed by NMR spectroscopy.
55. Luche, J.-L. J. Am. Chem. Soc. 1978, 100, 2226-2227.
56. Gannon, F. W.; House, H. O. Org. Syntheses 1960, 40, 41-42.
57. Woods, G. F.; Tucker, I. W. J. Am. Chem. Soc. 1948, 70, 2174-2177.
58. Mori, K.; Uchida, M.; Matsui, M. Tetrahedron 1977, 33, 385-387.
59. Tetrahydrofuran was probably released in this reaction which was under investigation.
60. Rothman, E. S.; Serota, S.; Perlstein, T.; Swern, D. J. Org. Chem. 1962, 27, 3123-3127. Wang, Y.-F.; Lalonde, J. L.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200-7205.
61. Rothman, E. S.; Serota, S.; Perlstein, T.; Swern, D. J. Org. Chem. 1962, 27, 3123-3127. Wang, Y.-F.; Lalonde, J. L.; Momongan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200-7205.
62. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299.
63. Small excesses of isopropenyl hexanoate were used in these reactions to allow an easier separation of the products. Care was taken that water was absent from the reaction mixture in order to ensure that isopropenyl hexanoate was still present when the reaction was stopped. If the isopropenyl hexanoate was totally consumed, a decrease in the enantiomeric ratio was observed, probably because the bicycloheptyl hexanoate had become the acylating agent.
64. 38 and its absolute configuration was proposed on the basis of chiroptical properties. A chemical correlation was made between this ethylcyclohexenol and a compound with a known absolute configuration because some discrepancies between the specific rotation sign and the absolute configuration were noticed in this family of 3-substituted cyclohex-2-enols: Aranda, G.; Bertranne, M.; Azerad, R.; Maurs, M. Tetrahedron: Asymmetry 1995, 6, 675-678.
65. Tamura, M.; Kochi, J. Synthesis 1971, 303-305.
66. Mori, K.; Tamada, S.; Uchida, M.; Mizumachi, N.; Tachibana, Y.; Matsui, M. Tetrahedron 1978, 34, 1901-1905.
67. For recent reports of the enantioselectivity of Candida antarctica lipase for the 'R'-isomer see: Forró, E.; Kanerva, L. T.; Fülöp, F. Tetrahedron: Asymmetry 1998, 9, 513-520; Conti, P.; Dallanoce, C.; De Amici, M.; De Micheli, C.; Carrea, G.; Zambianchi, F. Tetrahedron: Asymmetry 1998, 9, 657-665; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765-780; Conde, S.; Fierros, M.; Rodríguez-Franco, M. I.; Puig, C. Tetrahedron: Asymmetry 1998, 9, 2229-2232; Bit, C.; Mitrochkine, A. A.; Gil, G.; Pierrot, M.; Réglier, M. Tetrahedron: Asymmetry 1998, 9, 3263-3273. For a deviation from this rule see: Adam, W.; Díaz, M. T.; Saha-Möller, C. R. Tetrahedron: Asymmetry 1998, 9, 791-796.
68. For recent reports of the enantioselectivity of Candida antarctica lipase for the 'R'-isomer see: Forró, E.; Kanerva, L. T.; Fülöp, F. Tetrahedron: Asymmetry 1998, 9, 513-520; Conti, P.; Dallanoce, C.; De Amici, M.; De Micheli, C.; Carrea, G.; Zambianchi, F. Tetrahedron: Asymmetry 1998, 9, 657-665; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765-780; Conde, S.; Fierros, M.; Rodríguez-Franco, M. I.; Puig, C. Tetrahedron: Asymmetry 1998, 9, 2229-2232; Bit, C.; Mitrochkine, A. A.; Gil, G.; Pierrot, M.; Réglier, M. Tetrahedron: Asymmetry 1998, 9, 3263-3273. For a deviation from this rule see: Adam, W.; Díaz, M. T.; Saha-Möller, C. R. Tetrahedron: Asymmetry 1998, 9, 791-796.
69. For recent reports of the enantioselectivity of Candida antarctica lipase for the 'R'-isomer see: Forró, E.; Kanerva, L. T.; Fülöp, F. Tetrahedron: Asymmetry 1998, 9, 513-520; Conti, P.; Dallanoce, C.; De Amici, M.; De Micheli, C.; Carrea, G.; Zambianchi, F. Tetrahedron: Asymmetry 1998, 9, 657-665; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765-780; Conde, S.; Fierros, M.; Rodríguez-Franco, M. I.; Puig, C. Tetrahedron: Asymmetry 1998, 9, 2229-2232; Bit, C.; Mitrochkine, A. A.; Gil, G.; Pierrot, M.; Réglier, M. Tetrahedron: Asymmetry 1998, 9, 3263-3273. For a deviation from this rule see: Adam, W.; Díaz, M. T.; Saha-Möller, C. R. Tetrahedron: Asymmetry 1998, 9, 791-796.
70. For recent reports of the enantioselectivity of Candida antarctica lipase for the 'R'-isomer see: Forró, E.; Kanerva, L. T.; Fülöp, F. Tetrahedron: Asymmetry 1998, 9, 513-520; Conti, P.; Dallanoce, C.; De Amici, M.; De Micheli, C.; Carrea, G.; Zambianchi, F. Tetrahedron: Asymmetry 1998, 9, 657-665; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765-780; Conde, S.; Fierros, M.; Rodríguez-Franco, M. I.; Puig, C. Tetrahedron: Asymmetry 1998, 9, 2229-2232; Bit, C.; Mitrochkine, A. A.; Gil, G.; Pierrot, M.; Réglier, M. Tetrahedron: Asymmetry 1998, 9, 3263-3273. For a deviation from this rule see: Adam, W.; Díaz, M. T.; Saha-Möller, C. R. Tetrahedron: Asymmetry 1998, 9, 791-796.
71. For recent reports of the enantioselectivity of Candida antarctica lipase for the 'R'-isomer see: Forró, E.; Kanerva, L. T.; Fülöp, F. Tetrahedron: Asymmetry 1998, 9, 513-520; Conti, P.; Dallanoce, C.; De Amici, M.; De Micheli, C.; Carrea, G.; Zambianchi, F. Tetrahedron: Asymmetry 1998, 9, 657-665; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765-780; Conde, S.; Fierros, M.; Rodríguez-Franco, M. I.; Puig, C. Tetrahedron: Asymmetry 1998, 9, 2229-2232; Bit, C.; Mitrochkine, A. A.; Gil, G.; Pierrot, M.; Réglier, M. Tetrahedron: Asymmetry 1998, 9, 3263-3273. For a deviation from this rule see: Adam, W.; Díaz, M. T.; Saha-Möller, C. R. Tetrahedron: Asymmetry 1998, 9, 791-796.
72. For recent reports of the enantioselectivity of Candida antarctica lipase for the 'R'-isomer see: Forró, E.; Kanerva, L. T.; Fülöp, F. Tetrahedron: Asymmetry 1998, 9, 513-520; Conti, P.; Dallanoce, C.; De Amici, M.; De Micheli, C.; Carrea, G.; Zambianchi, F. Tetrahedron: Asymmetry 1998, 9, 657-665; Ziegler, T.; Bien, F.; Jurisch, C. Tetrahedron: Asymmetry 1998, 9, 765-780; Conde, S.; Fierros, M.; Rodríguez-Franco, M. I.; Puig, C. Tetrahedron: Asymmetry 1998, 9, 2229-2232; Bit, C.; Mitrochkine, A. A.; Gil, G.; Pierrot, M.; Réglier, M. Tetrahedron: Asymmetry 1998, 9, 3263-3273. For a deviation from this rule see: Adam, W.; Díaz, M. T.; Saha-Möller, C. R. Tetrahedron: Asymmetry 1998, 9, 791-796.
73. For crystallographic data of lipase B from Candida antarctica which reveal a stereospecific pocket for secondary alcohols see: Uppenberg, J.; Öhrner, N.; Norin, M.; Hult, K.; Kleywegt, G. J.; Patkar, S.; Waagen, V.; Anthonsen, T.; Jones, T. A. Biochemistry 1995, 34, 16838-16851.
74. Gupta, A. K.; Kazlauskas, R. J. Tetrahedron: Asymmetry 1993, 4, 879-888.
75. For a hydrolase specific 'S'-enantiomer of open chain secondary alcohols see: Lloyd, R. C.; Dickman, M.; Jones, J. B. Tetrahedron: Asymmetry 1998, 9, 551-561.
76. (a) Carrea, G.; Danieli, B.; Palmisano, G.; Riva, S.; Santagostino, M. Tetrahedron: Asymmetry 1992, 3, 775-784.
77. (b) Satoh, T.; Motohashi, S.; Tokutake, N.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1992, 65, 2966-2973
78. Dauben, W. G.; Shaffer, G. W.; Vietmeyer, N. D. J. Org. Chem. 1969, 33, 4060-4069. Jacquesy, R.; Patoiseau, J. F. Bull. Soc. Chim. Fr. 1978, 255-262.
79. Dauben, W. G.; Shaffer, G. W.; Vietmeyer, N. D. J. Org. Chem. 1969, 33, 4060-4069. Jacquesy, R.; Patoiseau, J. F. Bull. Soc. Chim. Fr. 1978, 255-262.
80. Inokuchi, T.; Tsuji, M.; Kawafuchi, H.; Torii, S. J. Org. Chem. 1991, 56, 5945-5948.
81. Jubert, C.; Knochel, P. J. Org. Chem. 1992, 57, 5425-5431.
82. Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181-5183.