Enzymatic resolution of endo-bicyclo[4.1.0]heptan-2-ols

Tetrahedron Letters

Volumn 38, Issue 49, 1997, Pages 8503-8506

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

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

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

ARTICLE; CHEMICAL REACTION; ENANTIOMER; ESTERIFICATION; REACTION ANALYSIS;

CANDIDA ANTARCTICA;

EID: 0030713385     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10299-4     Document Type: Article

References (33)

1. a) Collum, D.B.; Still, W.C.; Mohamadi, F. J. Am. Chem. Soc. 1986, 108, 2094-2096.
2. b) Batey, R.A.; Harline, J.D.; Motherwell, W.B. Tetrahedron 1996, 52, 11421-11444.
3. c) Clive, D.L.J.; Daigneault, S. J. Org. Chem. 1991, 56, 3801-3814.
4. For an example of an optically active bicyclo[n.1.0]alkan-2-ol isolated from a natural source see: Hiyamoto, T.; Ebisawa, Y.; Higuchi, R. Tetrahedron Lett. 1995, 36, 6073-6074.
5. a) Hill, R.K.; Morgan, J.W. J. Org. Chem. 1968, 33, 927-928.
6. b) Barbachyn, M.R.; Johnson, C.R.; Glick, M.D. J. Org. Chem. 1984, 49, 2746-2748.
7. For other examples of lipase catalyzed preparation of optically active cyclopropyl methyl alcohols 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 ; 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.
8. For other examples of lipase catalyzed preparation of optically active cyclopropyl methyl alcohols 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 ; 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.
9. For other examples of lipase catalyzed preparation of optically active cyclopropyl methyl alcohols 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 ; 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.
10. For other examples of lipase catalyzed preparation of optically active cyclopropyl methyl alcohols 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 ; 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.
11. For other examples of lipase catalyzed preparation of optically active cyclopropyl methyl alcohols 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 ; 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.
12. For other examples of lipase catalyzed preparation of optically active cyclopropyl methyl alcohols 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 ; 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.
13. For other examples of lipase catalyzed preparation of optically active cyclopropyl methyl alcohols 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 ; 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.
14. 2O: 80/20) (Yield: 75-80%).
15. 2O : 93/7) (Yield : 65-75%).
16. ® were used, they were purchassed from Novo Nordiste.
17. ® (48 mg) the above conditions were used. c) 1 mmol of chloroacetate 3 was treated with 100 mg of dry 1-propanol and 300 mg of lipase in 2 mL of dry tBuOMe.
18. 2O : 85/15 then 70/30).
19. 11) the singlets of the methyl protons linked to the cyclopropane were moved from 1.13 to 4.32 ppm (1S,2R,6R) and 4.24 ppm (1R,2S,6S); For 3c the singlets of the methyl protons were moved from 1.04 to 2.48 ppm (1R,2S,6S) and 2.42 ppm (1S,2R,6R).
20. 2).
21. 2).
22. 2O).
23. Enantiomeric excess was termined by HPLC of the corresponding phenyl carbamate on a 250mm × 4.5mm Chiralcel OD-H column (eluent : hexane/isopropanol : 85/15) ; Flow rate : 1 ml/min): Retention time : 1a-(1R,2S,6S)-phenylurethane : 16 min; 1a-(1S,2R,6R)-phenylurethane : 21 min.
24. Enantiomeric excess were determined by GLC on a 25m × 0.33mm ID CYDEX B column (Flow carrier: He, P = 0.8 Bar, 65°C). Retention time 1b-(1R,2S,65) : 24 min; 1b-(1S,2B,6R) : 20 min; 1c-(1R,2S,6S) : 25 min; 1c-(1R,2R,6R) : 34 min.
25. p).
26. p))], see: Chen, C.S.; Fujimoto, Y.; Girdaukas, G.; Sih C. J. J. Am. Chem. Soc. 1982, 104, 7294-7298.
27. The influence of the acyl chain length on the enantiomeric ratio of kinetic resolution of linear secondary alcohols in the presence of Lipozyme was reported: Sonnet, P.E. J. Org. Chem. 1987, 52, 3477-3479.
28. 7 (for the latter) catalyzed transesterification of isopropenyl acetate with the racemic alcohol.
29. Winstein, J.; Sonneberg, J.; Devries, L. J. Am. Chem. Soc. 1959, 81, 6523-6524; Dauben, W.G.; Berezin, G.H. J. Am. Chem. Soc. 1963, 85, 468-472. For a review on "Substrate-directable chemical reactions" where are reported various examples of hydroxyl directed cyclopropanation of allylic alcohols, see: Hoveyda, A.H.; Evans, D.A.; Fu, G.C. Chem. Rev. 1993, 93, 1307-1370.
30. Winstein, J.; Sonneberg, J.; Devries, L. J. Am. Chem. Soc. 1959, 81, 6523-6524; Dauben, W.G.; Berezin, G.H. J. Am. Chem. Soc. 1963, 85, 468-472. For a review on "Substrate-directable chemical reactions" where are reported various examples of hydroxyl directed cyclopropanation of allylic alcohols, see: Hoveyda, A.H.; Evans, D.A.; Fu, G.C. Chem. Rev. 1993, 93, 1307-1370.
31. Winstein, J.; Sonneberg, J.; Devries, L. J. Am. Chem. Soc. 1959, 81, 6523-6524; Dauben, W.G.; Berezin, G.H. J. Am. Chem. Soc. 1963, 85, 468-472. For a review on "Substrate-directable chemical reactions" where are reported various examples of hydroxyl directed cyclopropanation of allylic alcohols, see: Hoveyda, A.H.; Evans, D.A.; Fu, G.C. Chem. Rev. 1993, 93, 1307-1370.
32. Denmark, S.E.; Edwards, J.P. J. Org. Chem. 1991, 56, 6974-6981.
33. Miyano, S.; Izumi, Y.; Fujii, H.; Hashimoto, H. Synthesis 1977, 700-701.