Enzymatic resolution of bicyclo[n.1.0]alkan-1-ols derivatives: Preparation of optically active α-substituted α-methylcycloalkanones

Tetrahedron

Volumn 54, Issue 27, 1998, Pages 7749-7764

  Morisson, V ^a   Barnier, J P ^a   Blanco, L ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CYCLOALKANOL DERIVATIVE; ENZYME;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ESTERIFICATION; PRIORITY JOURNAL;

EID: 0032474810     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00411-6     Document Type: Article

References (63)

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6. 6. Some indirect methods should allow also the preparation of optically active α,α-disubstituted cycloalkanones: From optically active 3-hydroxyalkanoates: Fráter, G.; Müller, U.; Günther, W. Tetrahedron 1984, 40, 1269-1277. From optically active α-ketoepoxides: Marshall, J.A.; Flynn, K.E. J. Am. Chem. Soc. 1982, 104, 7430-7435. From optically active α′,α′-disubstituted cycloalkenones: Romo, D.; Meyers, A.I. Tetrahedron 1991, 47, 9503-9569.
7. 6. Some indirect methods should allow also the preparation of optically active α,α-disubstituted cycloalkanones: From optically active 3-hydroxyalkanoates: Fráter, G.; Müller, U.; Günther, W. Tetrahedron 1984, 40, 1269-1277. From optically active α-ketoepoxides: Marshall, J.A.; Flynn, K.E. J. Am. Chem. Soc. 1982, 104, 7430-7435. From optically active α′,α′-disubstituted cycloalkenones: Romo, D.; Meyers, A.I. Tetrahedron 1991, 47, 9503-9569.
8. 6. Some indirect methods should allow also the preparation of optically active α,α-disubstituted cycloalkanones: From optically active 3-hydroxyalkanoates: Fráter, G.; Müller, U.; Günther, W. Tetrahedron 1984, 40, 1269-1277. From optically active α-ketoepoxides: Marshall, J.A.; Flynn, K.E. J. Am. Chem. Soc. 1982, 104, 7430-7435. From optically active α′,α′-disubstituted cycloalkenones: Romo, D.; Meyers, A.I. Tetrahedron 1991, 47, 9503-9569.
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18. 11. Pinheiro, S.; Guingant, A.; Desmaële, D.; d'Angelo, J. Tetrahedron: Asymm. 1992, 3, 1003-1006. Gaidarova, E.L.; Grishina, G.V. Synlett 1992, 89-93. Guingant, A.; Hammami, H. Tetrahedron: Asymm. 1993, 4, 25-26. Felk, A.; Revial, G.; Viossat, B.; Lemoine, P.; Pfau, M. Tetrahedron: Asymm. 1994, 5, 1459-1462. Cavé, C.; Daley, V.; d'Angelo, J.; Guingant, A. Tetrahedron: Asymm. 1995, 6, 79-82. Jabin, L; Revial, G.; Thomas, A.; Lemoine, P.; Pfau M. Tetrahedron: Asymm. 1995, 6, 1795-1812. Jabin, I.; Revial, G.; Mellouk, K.; Pfau M. Tetrahedron: Asymm. 1997, 8, 1101-1109. Alves, J.C.F.; Simas, A.B.C.; Costa, P.R.R.; d'Angelo, J. Tetrahedron: Asymm. 1997, 8, 1963-1966. Hamzaoui, M.; Provot, O.; Grégoire, F.; Riche, C.; Chiaroni, A.; Gay, F.; Moskowitz, H.; Mayrargue, J. Tetrahedron: Asymm. 1997, 8, 2085-2088.
19. 11. Pinheiro, S.; Guingant, A.; Desmaële, D.; d'Angelo, J. Tetrahedron: Asymm. 1992, 3, 1003-1006. Gaidarova, E.L.; Grishina, G.V. Synlett 1992, 89-93. Guingant, A.; Hammami, H. Tetrahedron: Asymm. 1993, 4, 25-26. Felk, A.; Revial, G.; Viossat, B.; Lemoine, P.; Pfau, M. Tetrahedron: Asymm. 1994, 5, 1459-1462. Cavé, C.; Daley, V.; d'Angelo, J.; Guingant, A. Tetrahedron: Asymm. 1995, 6, 79-82. Jabin, L; Revial, G.; Thomas, A.; Lemoine, P.; Pfau M. Tetrahedron: Asymm. 1995, 6, 1795-1812. Jabin, I.; Revial, G.; Mellouk, K.; Pfau M. Tetrahedron: Asymm. 1997, 8, 1101-1109. Alves, J.C.F.; Simas, A.B.C.; Costa, P.R.R.; d'Angelo, J. Tetrahedron: Asymm. 1997, 8, 1963-1966. Hamzaoui, M.; Provot, O.; Grégoire, F.; Riche, C.; Chiaroni, A.; Gay, F.; Moskowitz, H.; Mayrargue, J. Tetrahedron: Asymm. 1997, 8, 2085-2088.
20. 11. Pinheiro, S.; Guingant, A.; Desmaële, D.; d'Angelo, J. Tetrahedron: Asymm. 1992, 3, 1003-1006. Gaidarova, E.L.; Grishina, G.V. Synlett 1992, 89-93. Guingant, A.; Hammami, H. Tetrahedron: Asymm. 1993, 4, 25-26. Felk, A.; Revial, G.; Viossat, B.; Lemoine, P.; Pfau, M. Tetrahedron: Asymm. 1994, 5, 1459-1462. Cavé, C.; Daley, V.; d'Angelo, J.; Guingant, A. Tetrahedron: Asymm. 1995, 6, 79-82. Jabin, L; Revial, G.; Thomas, A.; Lemoine, P.; Pfau M. Tetrahedron: Asymm. 1995, 6, 1795-1812. Jabin, I.; Revial, G.; Mellouk, K.; Pfau M. Tetrahedron: Asymm. 1997, 8, 1101-1109. Alves, J.C.F.; Simas, A.B.C.; Costa, P.R.R.; d'Angelo, J. Tetrahedron: Asymm. 1997, 8, 1963-1966. Hamzaoui, M.; Provot, O.; Grégoire, F.; Riche, C.; Chiaroni, A.; Gay, F.; Moskowitz, H.; Mayrargue, J. Tetrahedron: Asymm. 1997, 8, 2085-2088.
21. 11. Pinheiro, S.; Guingant, A.; Desmaële, D.; d'Angelo, J. Tetrahedron: Asymm. 1992, 3, 1003-1006. Gaidarova, E.L.; Grishina, G.V. Synlett 1992, 89-93. Guingant, A.; Hammami, H. Tetrahedron: Asymm. 1993, 4, 25-26. Felk, A.; Revial, G.; Viossat, B.; Lemoine, P.; Pfau, M. Tetrahedron: Asymm. 1994, 5, 1459-1462. Cavé, C.; Daley, V.; d'Angelo, J.; Guingant, A. Tetrahedron: Asymm. 1995, 6, 79-82. Jabin, L; Revial, G.; Thomas, A.; Lemoine, P.; Pfau M. Tetrahedron: Asymm. 1995, 6, 1795-1812. Jabin, I.; Revial, G.; Mellouk, K.; Pfau M. Tetrahedron: Asymm. 1997, 8, 1101-1109. Alves, J.C.F.; Simas, A.B.C.; Costa, P.R.R.; d'Angelo, J. Tetrahedron: Asymm. 1997, 8, 1963-1966. Hamzaoui, M.; Provot, O.; Grégoire, F.; Riche, C.; Chiaroni, A.; Gay, F.; Moskowitz, H.; Mayrargue, J. Tetrahedron: Asymm. 1997, 8, 2085-2088.
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24. 11. Pinheiro, S.; Guingant, A.; Desmaële, D.; d'Angelo, J. Tetrahedron: Asymm. 1992, 3, 1003-1006. Gaidarova, E.L.; Grishina, G.V. Synlett 1992, 89-93. Guingant, A.; Hammami, H. Tetrahedron: Asymm. 1993, 4, 25-26. Felk, A.; Revial, G.; Viossat, B.; Lemoine, P.; Pfau, M. Tetrahedron: Asymm. 1994, 5, 1459-1462. Cavé, C.; Daley, V.; d'Angelo, J.; Guingant, A. Tetrahedron: Asymm. 1995, 6, 79-82. Jabin, L; Revial, G.; Thomas, A.; Lemoine, P.; Pfau M. Tetrahedron: Asymm. 1995, 6, 1795-1812. Jabin, I.; Revial, G.; Mellouk, K.; Pfau M. Tetrahedron: Asymm. 1997, 8, 1101-1109. Alves, J.C.F.; Simas, A.B.C.; Costa, P.R.R.; d'Angelo, J. Tetrahedron: Asymm. 1997, 8, 1963-1966. Hamzaoui, M.; Provot, O.; Grégoire, F.; Riche, C.; Chiaroni, A.; Gay, F.; Moskowitz, H.; Mayrargue, J. Tetrahedron: Asymm. 1997, 8, 2085-2088.
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29. 14. Other specific enzymatic methods are described: esterase-catalyzed hydrolysis of 2,2-bis(acetoxymethyl)cyclopentanone: Suemune, H.; Harabe, T.; Xie, Z.F.; Sakai, K. Chem. Pharm. Bull. 1988, 36, 4337-4344; Lipase-catalyzed hydrolysis of enol acetates: Sugai, T.; Kakeya, H.; Ohta, H.; Morooka, M.; Ohba, S. Tetrahedron 1989, 45, 6135-6144.
30. 14. Other specific enzymatic methods are described: esterase-catalyzed hydrolysis of 2,2-bis(acetoxymethyl)cyclopentanone: Suemune, H.; Harabe, T.; Xie, Z.F.; Sakai, K. Chem. Pharm. Bull. 1988, 36, 4337-4344; Lipase-catalyzed hydrolysis of enol acetates: Sugai, T.; Kakeya, H.; Ohta, H.; Morooka, M.; Ohba, S. Tetrahedron 1989, 45, 6135-6144.
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35. 16 With the indicated inorganic acid mixture the crude alkylated cycloalkanone was obtained free of acetic acid and was more easily purified.
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43. 2I)2] or to suppose a catalytic influence of oxygen on the reaction of the organozinc reagents with the olefin.
44. 29
45. 26. Careful neutralisation of the reaction mixture before evaporation of methanol gave a more reliable method to obtain the bicycloalkanol free of a-methylketone resulting from cyclopropanic bond cleavage which is easier in acid or basic medium.
46. 27. These chloroacetates were mixed with regioisomers which came from the minor less substituted silyl enol ether formed during the synthesis of 2.
47. 28. This preparation of Lipase from Mucor miehei on a resin was purchased from Novo Nordisk A/S.
48. 29. A radical cleavage of the bicyclohexanol which presents higher strain energy than the homologs was postulated. This reaction is under investigation.
49. 30. Chen, C.-S.; Wu, S.-H.; Girdaukas, G.; Sih, C.J. J. Am. Chem. Soc. 1987, 109, 2812-2817. c = ees/(ees+eep). E = Ln[(1-ees)(eep/(ees+eep))]/Ln[(1+ees)(eep/(ees+eep))].
50. 31. The transesterification of 51 was also attempted in the presence of other lipases. With the lipases from Candida lipolytica, from Pseudomonas fluorescens and from Chromobacterium viscosum no reaction with 1-propanol were observed after 3 days at 36°C (these results confirm that the uncatalyzed transesterification was not a competitive process in our conditions). With the lipase from Candida rugosa, the lipase from Pseudomonas cepacia and the pig pancreatic lipase the reaction has occurred and the conversions were respectively 7% (after 3 days), 13% (after 3 days) and 24% (after 4 days) using the same ratio of the enzyme weight to the chloroacetate weight than that of the Lipozyme®-catalyzed reaction.
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