Optically active 1,3-dioxolane-4-methanols. Lipase-catalysed acylation of racemic ketals and diastereomeric acetals

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 3037-3046

  Vänttinen, Eero ^a   Kanerva, Liisa T ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; DRUG SYNTHESIS; ENZYME ACTIVITY; PRIORITY JOURNAL; PSEUDOMONAS; REACTION ANALYSIS;

EID: 0030271656     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00394-1     Document Type: Article

References (30)

1. 1. Theil, F. Chem. Rev. 1995, 95, 2203.
2. 2. Kanerva, L.T. In Enzymatic Reactions in Organic Media, Koskinen, A.M.P. and Klibanov, A.M., Eds., Chapman & Hall, London, 1996, Ch.7, 170.
3. 3. Sih, C.J.; Girdaukas, G.; Chen, C.-S.; Sih, J.C. In Enzymatic Reactions in Organic Media, Koskinen, A.M.P. and Klibanov, A.M., Eds., Chapman & Hall, London, 1996, Ch. 5, p.94.
4. 4. Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447.
5. 5. Chen, C.-S.; Sih, C.J. Angew. Chem. Int. Ed. Engl. 1989, 28, 695.
6. 6. Ladner, W.E.; Whitesides, G.M. J. Am. Chem. Soc. 1984, 106, 7250.
7. 7. Fuganti, C.; Grasselli, P.; Servi, S.; Lazzarini, A.; Casati, P. J. Chem. Soc., Chem. Commun. 1987, 538.
8. 8. Wang, Y.-F.; Lalonde, J.J.; Momongan, M.; Bergbreiter, D.E.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200.
9. 9. Terao, Y.; Tsuji, K.; Murata, M.; Achiwa, K.; Nishio, T.; Watanabe, N.; Seto, K. Chem. Pharm. Bull. 1989, 37, 1653.
10. 10. Maconi, E.; Gualandris, R.; Aragozzini, F. Biotechnol. Lett. 1990, 12, 415.
11. 11. Partali, V.; Melbye, A.G.; Alvik, T.; Anthonsen, T. Tetrahedron: Asymmetry 1992, 3, 65.
12. 12. Parmar, V.S.; Prasad, A.K.; Singh, P.K.; Gupta, S. Tetrahedron: Asymmetry 1992, 3, 1395.
13. 13. Bosetti, A.; Bianchi, D.; Cesti, P.; Golini, P. Biocatalysis 1994, 9, 71.
14. 14. Pallavicini, M.; Valoti, E.; Villa, L.; Piccolo, O. J. Org. Chem. 1994, 59, 1751.
15. 15. Phung, A.N.; Braun, J.; Le Goffic, F. Synth. Commun. 1995, 25, 1783.
16. 16. Vänttinen, E.; Kanerva, L.T. J. Chem. Soc., Perkin 1 1994, 3459.
17. 17. Carbonate 1 was prepared from glycerol with diethyl carbonate in the presence of NaOH. Pfaendler, H.R.; Müller, F.X. Synthesis 1992, 350. Compounds 2-7 were prepared by the acid-catalysed ketalization of glycerol. Org. Synth. Coll. VoI III 1955, 502. Aldehydes corresponding to compounds 8-13 produce the mixture of the dioxan-5-ol and dioxolane-4-methanol under the same conditions.
18. 17. Carbonate 1 was prepared from glycerol with diethyl carbonate in the presence of NaOH. Pfaendler, H.R.; Müller, F.X. Synthesis 1992, 350. Compounds 2-7 were prepared by the acid-catalysed ketalization of glycerol. Org. Synth. Coll. VoI III 1955, 502. Aldehydes corresponding to compounds 8-13 produce the mixture of the dioxan-5-ol and dioxolane-4-methanol under the same conditions.
19. 3-catalysed addition of benzaldehyde to epichlorohydrin. Wershofen, S.; Classen, A.; Scharf, H.-D. Liebigs. Ann. Chem. 1989, 9. 12+13 was prepared analogously from pivalaldehyde and epichlorohydrin except that sodium butyrate was replaced by sodium benzoate and the cis/trans alcohol was released by saponification of the benzoate ester with NaOH.
20. trans
21. 20. The acetal and ketal exchange reactions were performed between (R)-solketal butyrate (66 % ee) and the carbonyl compound in the presence of acid Amberlyst 15 ion-exchange resin. Acyl migration was insignificant as indicated by only slight racemication.
22. 21. For 8 and 9 see Inch, T. D.; Williams, N. J. Chem. Soc. 1970, 263. For 12 and 13 see Carman, R. M.; Kibby, J. J. Aust. J. Chem. 1976, 29, 1761.
23. 21. For 8 and 9 see Inch, T. D.; Williams, N. J. Chem. Soc. 1970, 263. For 12 and 13 see Carman, R. M.; Kibby, J. J. Aust. J. Chem. 1976, 29, 1761.
24. 0-D were used (see ref. 19). (10) (equation presented) (11) (equation presented) (12) (equation presented) (13) (equation presented) (14) (equation presented) (15) (equation presented) (16) (equation presented) (17) (equation presented)
25. 23. Kim, M.-J.; Lee, I.S.; Synlett 1993, 767.
26. 24. Bisht, K.S.; Parmar, V.S.; Crout, D.H.G. Tetrahedron: Asymmetry 1993, 4, 957.
27. 25. Sugai, T.; Yokochi, T.; Watanabe, N.; Ohta, H. Tetrahedron 1991, 47, 7227.
28. 26. Franssen, M.C.R.; Boavida dos Santos, P.M.A.C.; Camacho Mondril, N.L.F.L.; de Groot, A. Pure Appl. Chem. 1992, 64, 1089.
29. 27. Kazlauskas, R.J.; Weissfioch, A.N.E. J. Org. Chem. 1995, 60, 6959.
30. 28. Initial composition and the enzymatic reaction was analyzed by the GLC method after derivatization with acetic and propionic anhydride, respectively (ref. 19). Total conversion was calculated by equation: (equation presented), the term re designating ring isomeric excess with respect to the ring isomer cited in the superscript, the subscripts as in ref. 22. It is assumed that the isomers have identical responses in FID-detection.