Lipase catalyzed resolution of α-hydroxymethyl sulfones. Determination of absolute configuration by semiempirical calculation of CD spectra and verification by X-ray structure analysis

Tetrahedron Asymmetry

Volumn 8, Issue 18, 1997, Pages 3111-3123

  Gais, Hans Joachim ^a   Von Der Weiden, Ingo ^a   Fleischhauer, Jörg ^a   Esser, Josef ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; BURKHOLDERIA CEPACIA; CANDIDA; CIRCULAR DICHROISM; DRUG PURIFICATION; ENANTIOMER; ESTERIFICATION; IN VITRO STUDY; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0030923461     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00377-7     Document Type: Article

References (54)

1. (a) Gais; H.-J. In Enzyme Catalysis in Organic Synthesis Drauz, K.; Waldmann, H., Eds., VCH, Weinheim, 1995, Vol. I, p. 165.
2. (b) Theil, F. Chem. Rev. 1995, 95, 2203.
3. For recent examples, see: (a) Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959.
4. (b) Kang, S.-K.; Jeon, J.-H.; Yamaguchi, T.; Hong, R.-K.; Ko, B.-S. Tetrahedron: Asymmetry 1995, 6, 97.
5. (c) Ono, M.; Ogura, Y.; Hatogai, K.; Akita, H. Tetrahedron: Asymmetry 1995, 6, 1829.
6. (d) Altenbach, H.-J.; Merhof, G. F.; Brauer, D. J. Tetrahedron: Asymmetry 1996, 7, 2493.
7. (e) Lampe, T. F. J.; Hoffmann, H. M. R. Tetrahedron: Asymmetry 1996, 7, 2889.
8. (f) Di Bussolo, V.; Catelani, G.; Mastrorilli, E.; Di Bugno, C.; Giorgi, R. Tetrahedron: Asymmetry 1996, 7, 3585.
9. (a) Ehrler, J.; Seebach, D. Liebigs Ann. Chem. 1990, 379.
10. (b) Hultin, P. G.; Jones, J. B. Tetrahedron Lett. 1992, 33, 1399.
11. (c) Wimmer, Z. Tetrahedron 1992, 39, 8431.
12. (d) Guanti, G.; Banfi, L.; Narisano, E. J. Org. Chem. 1992, 57, 1540.
13. (e) Naemura, K.; Fukuda, R.; Takahashi, N.; Konishi, M.; Hirose, Y.; Tobe, Y. Tetrahedron: Asymmetry 1993, 4, 911.
14. (f) Carrea, G.; De Amici, M.; De Micheli, C.; Liverani, P.; Carnielli, M.; Riva, S. Tetrahdron: Asymmetry 1993, 4, 1063.
15. (g) Xie, Z.-F.; Suemune, H.; Sakai, K. Tetrahedron: Asymmetry 1993, 4, 973.
16. (h) Ferraboschi, P.; Casati, S.; Degrandi, S.; Grisenti, P.; Santiello, E. Biocatalysis 1994, 10, 279.
17. (i) Theil, T.; Lemke, K.; Ballschuh, S.; Kunath, A.; Schick, H. Tetrahedron: Asymmetry 1995, 6, 1323.
18. (j) Naemura, K.; Fukuda, R.; Murata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385.
19. For the lipase catalyzed resolution of secondary alcohols bearing a sulfonyl group, see: (a) Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Santaniello, E. J. Org. Chem. 1990, 55, 6214.
20. (b) Chinchilla, R.; Nájero, C.; Pardo, J.; Yus, M. Tetrahedron: Asymmetry 1990, 1, 575.
21. (c) Dominguez, E.; Carretero, J. C.; Fernandez-Mayoralas, A.; Conde, S. Tetrahedron Lett. 1991, 32, 5159.
22. (d) Carretero, J. C.; Dominguez, E. J. Org. Chem. 1992, 57, 3867.
23. For the lipase catalyzed resolution of a primary alcohol bearing a sulfonylmethyl group at the sterogenic center, see: Guevel, R.; Paquette, L. A. Tetrahedron: Asymmetry 1993, 4, 947.
24. Gais, H.-J.; Hellmann, G. J. Am. Chem. Soc. 1992, 114, 4439.
25. For a preliminary report of a part of this work, see: Gais, H.-J.; von der Weiden, I. Tetrahedron: Asymmetry 1996, 5, 1253.
26. Hurd, C. D.; Wilkinson, K. J. Am. Chem. Soc. 1949, 71, 3429.
27. Claesen, C. A. A.; Segers, R. P. A. M.; Tesser, G. I. Rec. Trav. Chim. Pays-Bas 1985, 104, 119.
28. For the synthesis of the S-phenyl analog of rac-6, see: Jung, J. H.; Lee, J. W.; Oh, D. Y. Tetrahedron Lett. 1995, 36, 923.
29. (a) Degueil-Castaing, M.; de Jeso, B.; Drouillard, S.; Maillard, B. Tetrahedron Lett. 1987, 28, 953.
30. (b) Wang, Y.-F.; Lalonde, J. J.; Momogan, M.; Bergbreiter, D. E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200.
31. (a) Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
32. (b) Rakels, J. L. L.; Straathof, A. J. J.; Heijnen, J. J. Enzyme Microb. Technol. 1993, 15, 1051.
33. (a) Rotticci, D.; Orrenius, C.; Hult, K.; Norin, T. Tetrahedron: Asymmetry 1997, 8, 359.
34. (b) Uppenberg, J.; Öhrner, N.; Norin, M.; Hult, K.; Kleywegt, G. J.; Patkar, S.; Waagen, V.; Anthonson, T.; Jones, T. A. Biochem. 1995, 34, 16838.
35. (a) Gais, H.-J.; Hemmerle, H. Tetrahedron Lett. 1987, 28, 3471.
36. (b) Gais, H.-J.; Hemmerle, H.; Kossek, S. Synthesis 1992, 169.
37. von der Weiden, I. Ph. D. Thesis, RWTH Aachen 1997.
38. (a) Bringmann, G.; Gulden, K. P.; Busse, H.; Fleischhauer, J.; Kramer, B.; Zobel, E. Tetrahedron 1993, 49, 3305.
39. (b) Fleischhauer, J.; Koslowski, A.; Kramer, B.; Zobel, E.; Bringmann, G.; Gulden, K. P.; Ortmann, T.; Peter, B. Z. Naturforsch. 1993, 48B, 140.
40. (c) Hoffmann, R. W.; Kahrs, B. C.; Schiffer, J.; Fleischhauer, J. J. Chem. Soc., Perkin Trans. 2 1996, 2407.
41. (a) Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8551.
42. (b) Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8566.
43. (c) Lii, J.-H.; Allinger, N. L. J. Am. Chem. Soc. 1989, 111, 8576.
44. Del Bene, J.; Jaffé, H. H. J. Chem. Phys. 1968, 48, 1807.
45. The programs DZDO and MCD3SP were written by J. W. Downing and J. Michl (University of Colorado at Boulder) and modified by J. Fleischhauer, W. Schleker and B. Kramer.
46. All excitations from the 13 highest occupied into the 13 lowest unoccupied molecular orbitals were taken into account.
47. Schellman, J. A. Chem. Rev. 1975, 75, 323.
48. The Gaussians were generated using a half bandwith of 10 nm.
49. i are the Boltzmann factor and the energy of the i-th local minimum, respectively. (b) The experimentally observed CD band occuring with very low intensity at λ=258 nm does not appear in our calculated CD spectrum. Perhaps more local minima have to be taken into account to reproduce this part of the spectrum.
50. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. [Fax: +44 (1223) 336033; Email: deposit@chemcrys.cam.ac.uk].
51. (a) Flack, H. D. Acta Cryst. 1983, A39, 876.
52. (b) Hall, S. R.; Flack, H. D.; Stewart, J. M., Eds. XTAL3.2 Reference Manual Universities of Western Australia, Geneva, and Maryland, Lamb, Perth, 1992.
53. (c) Subramanian, V.; Hall, S. R., GENSIN, XTAL3.2 Reference Manual, Hall, S. R.; Flack, H. D.; Stewart, J. M., Eds., Universities of Western Australia, Geneva, and Maryland, Lamb, Perth, 1992, p. 131.
54. (d) Hall, S. R., GENTAN, XTAL3.2 Reference Manual, Hall, S. R.; Flack, H. D.; Stewart, J. M., Eds., Universities of Western Australia, Geneva, and Maryland, Lamb, Perth, 1992, p. 139.