Preparation of enantiomerically pure α-hydroxymethyl S-tert-butyl sulfones by Candida antarctica lipase catalyzed resolution

Tetrahedron Asymmetry

Volumn 7, Issue 5, 1996, Pages 1253-1256

  Gais, Hans Joachim ^a   Von Der Weiden, Ingo ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

SULFONE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENZYME ACTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029992513     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00135-8     Document Type: Article

References (23)

1. (a) Gais, H.-J.; Hellmann, G.; Lindner, H.-J. Angew. Chem. 1990, 102, 96; Angew. Chem., Int. Ed. Engl. 1990, 29, 100.
2. (a) Gais, H.-J.; Hellmann, G.; Lindner, H.-J. Angew. Chem. 1990, 102, 96; Angew. Chem., Int. Ed. Engl. 1990, 29, 100.
3. (b) Gais, H.-J.; Hellmann, G. J. Am. Chem. Soc. 1992, 114, 4439.
4. Kozikowski, A. P.; Mugrage, B. B.; Li, C. S.; Felder L. Tetrahedron Lett. 1986, 27, 4817.
5. Tanikaga, R.; Hosoya, K.; Kaji, A. J. Chem. Soc. Perkin Trans. I 1988, 2397 and earlier work cited therein.
6. Thompson, C. M.; Green, D. L. C. Tetrahedron 1991, 47, 4223.
7. Jung, J. H.; Lee, J. W.; Oh, D. Y. Tetrahedron Lett. 1995, 36, 923.
8. Julia, M.; Uguen, D.; Callipolitis, A. Bull. Soc. Chim. Fr. 1976, 98, 519.
9. (a) Gais, H.-J.; Hemmerle, H. Tetrahedron Lett. 1987, 28, 3471.
10. (b) Gais, H.-J.; Hemmerle, H.; Kossek, S. Synthesis 1992, 169.
11. Gais, H.-J. In Enzyme Catalysis in Organic Synthesis, Drauz, K.; Waldmann, H., Eds.; VCH: Weinheim, 1995; Vol. I, p 165.
12. Chinchilla, R.; Najera, C.; Pardo, J.; Yus, M. Tetrahedron: Asymmetry 1990, 1, 575.
13. Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Santaniello, E. J. Org. Chem. 1990, 55, 6214.
14. Carretero, J. C.; Dominquez, E. J. Org. Chem. 1992, 57, 3867.
15. Guevel, R.; Paquette, L. A. Tetrahedron: Asymmetry 1993, 4, 947.
16. Hurd, C. D.; Wilkinson, K. J. Am. Chem. Soc. 1949, 71, 3429.
17. Claesen, C. A. A.; Segers, R. P. A. M.; Tesser, G. I. Rec. Trav. Chim. Pays-Bas 1985, 104, 119.
18. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
19. 2O), mp 81 °C.
20. Based on this result the absolute configuration of 3a-c and 4a-c was tentatively assigned as depicted in Scheme 2.
21. Uppenberg, J.; Öhrner, N.; Norin, M.; Hult, K.; Kleywegt, G. J.; Patkar, S.; Waagen, V.; Anthonson, T.; Jones, T. A. Biochem. 1995, 34, 16838.
22. Orrenius, C.; Norin, T.; Hult, K.; Carrea, G. Tetrahedron: Asymmetry 1995, 6, 3023.
23. 3)).