Volume 37, Issue 4 pp. 991-995

Article

Lipase-catalysed kinetic resolution of hydroxymethylchromanes^†

A. Czompa,

A. Czompa

Department of Organic Chemistry, University of Debrecen, P.O. Box 20, H-4010 Debrecen, Hungary

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T. Kovács,

T. Kovács

Department of Organic Chemistry, University of Debrecen, P.O. Box 20, H-4010 Debrecen, Hungary

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S. Antus,

S. Antus

Department of Organic Chemistry, University of Debrecen, P.O. Box 20, H-4010 Debrecen, Hungary

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A. Czompa,

A. Czompa

Department of Organic Chemistry, University of Debrecen, P.O. Box 20, H-4010 Debrecen, Hungary

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T. Kovács,

T. Kovács

Department of Organic Chemistry, University of Debrecen, P.O. Box 20, H-4010 Debrecen, Hungary

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S. Antus,

S. Antus

Department of Organic Chemistry, University of Debrecen, P.O. Box 20, H-4010 Debrecen, Hungary

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First published: 11 March 2009

https://doi.org/10.1002/jhet.5570370450

Citations: 6

^†

Dedicated to the Memory of Professor Raymond N. Castle

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Abstract

An effective kinetic resolution of hydroxymethylchromanes racemic 2a and 3a has been achieved by means of enantioselective transesterification with vinyl acetate in organic solvents. The alcohols (-)-R-2a and (-)-S-3a were obtained with high optical purities (94 and 98% ee) in 70% and 38% yields, respectively. The influence of the enzyme source and the character of the solvent on the enantioselectivity were studied.

References and Notes

1 C. H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon, Oxford (1994).
10.1016/B978-0-08-035941-0.50005-7
Google Scholar
2 K. Faber, Biotransformations in Organic Chemistry, Springer-Verlag, Berlin (1995).
10.1007/978-3-642-97607-0
Google Scholar
3 A. M. P. Koskinen and A. M. Klibanov (Eds.), Enzymatic Reactions in Organic Media, Blackie Academic, Glasgow (1996).
10.1007/978-94-011-0611-5
Google Scholar
4 A. M. Klibanov, Acc. Chem. Res., 23, 114 (1990).
10.1021/ar00172a004
CAS Web of Science® Google Scholar
5 S. Servi, Synthesis, 1 (1990).
Google Scholar
6 S. M. Roberts, K. Wiggins and K. Casy (Eds.), Preparative Biotransformations: Whole Cell and Isolated Enzymes in Organic Synthesis, John Wiley & Sons Ltd., New York (1993).
Google Scholar
7 S. Antus, Á. Gottsegen, J. Kajtár, T. Kovács, T. S. Tóth and H. Wagner, Tetrahedron Asymmetry, 339 (1993).
Google Scholar
8 F. J. Urban and B. S. Moore, J. Heterocyclic Chem., 29, 431 (1992).
10.1002/jhet.5570290223
CAS Web of Science® Google Scholar
9 C. Melchiorre, A. Minarini, V. Tumiatti, E. Giraldo, G. B. Schiavi and M. Turconi, Med. Chem. Res., 4, 140 (1993).
Google Scholar
10 C. Marot, C. Comoy, M. C. Viaud, M. C. Rettori, B. Pfeiffer, L. Morin-Allory and G. Guillaumet, Bioorg. Med. Chem. Lett., 6, 1077 (1996).
10.1016/0960-894X(96)00174-6
CAS Web of Science® Google Scholar
11 M. Payard, G. Mouysset, P. Tronche, P. Bastide, J. Bastide and M. J. Boas, Eur. J. Med. Chem. Chim. Ther., 20, 2, 117 (1985).
Google Scholar
12 R. P. Houghton, M. Voyle and R. Price, J. Chem. Soc. Perkin Trans. I., 5, 925 (1984).
10.1039/p19840000925
Web of Science® Google Scholar
13 G. Mouysset, M. Payard, G. Grassy, P. Tronche and H. Dabire, Eur. J. Med. Chem. Chim. Ther., 22, 539 (1987).
10.1016/0223-5234(87)90294-7
CAS Web of Science® Google Scholar
14 G. Broggini, F. Folcio, N. Sardone, M. Sonzogni and G. Zecchi, Tetrahedron Asymmetry, 7, 797 (1996).
10.1016/0957-4166(96)00076-6
CAS Web of Science® Google Scholar
15 S. Antus, E. Baitz-Gács, J. Kajtár, G. Snatzke and A. L. Tökés, Liebigs Ann. Chem., 497 (1994).
Google Scholar
16 B. Herradon and S. Valverde, Tetrahedron Asymmetry, 5, 1479 (1994).
10.1016/0957-4166(94)80118-5
CAS Web of Science® Google Scholar
17 H. Miyaoka, Y. Kajiwara, M. Hara, A. Suma and Y. Yamada, Tetrahedron Asymmetry, 10, 3189 (1999).
10.1016/S0957-4166(99)00304-3
CAS Web of Science® Google Scholar
18 M. D. Ennis and D. W. Old, Tetrahedron Lett., 33, 6283 (1992).
10.1016/S0040-4039(00)60953-X
CAS Web of Science® Google Scholar
19 M. D. Ennis and N. B. Ghatal, Tetrahedron Lett., 33, 6287 (1992).
10.1016/S0040-4039(00)60954-1
CAS Web of Science® Google Scholar
20 D. Mauleon, C. Lobato and G. Carganico, J. Heterocyclic Chem., 31, 57 (1994).
10.1002/jhet.5570310110
CAS Web of Science® Google Scholar
21 R. S. Cahn, C. Ingold and V. Prelog, Angew. Chem., 78, 413 (1966).
10.1002/ange.19660780803
Google Scholar
22 C-S. Chen, Y. Fujimoto, G. Girdaukas and C. J. Sih, J. Am. Chem. Soc., 104, 7294 (1982).
10.1021/ja00389a064
CAS Web of Science® Google Scholar

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Volume37, Issue4

July/August 2000

Pages 991-995

Lipase-catalysed kinetic resolution of hydroxymethylchromanes^†

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Lipase-catalysed kinetic resolution of hydroxymethylchromanes†

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Lipase-catalysed kinetic resolution of hydroxymethylchromanes^†