Actas de congresos
Bioreduction Of α-substituted 3,4-(methylenedioxy)-acetophenones By Rhodotorula Glutinis And Geotrichum Candidum
Registro en:
Brazilian Archives Of Biology And Technology. , v. 49, n. SPEC. ISS., p. 133 - 136, 2006.
15168913
2-s2.0-33748665020
Autor
Antunes H.
Fardelone L.C.
Rodrigues J.A.R.
Moran P.J.S.
Institución
Resumen
Enantioselective reductions of a-azido- and a-bromo-3,4-(methylenedioxy) acetophenones mediated by Rhodotorula glutinis and Geotrichum candidum afforded the corresponding alcohols, with complementary enantioselectivity, R and S respectively. The obtained (R)-alcohols are important raw materials for the preparation of valuable pharmaceutical catecholamines. 49 SPEC. ISS. 133 136 Ager, D.J., Prakash, I., Schaad, D.R., 1,2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis (1996) Chem. Rev., 96, pp. 835-875 Aleixo, L.M., Carvalho, M., Moran, P.J.S., Rodrigues, J.A.R., Hydride transfer versus electron transfer in the Baker's yeast reduction of a-haloacetophenones (1993) Bioorg. Med. Chem. Lett., 3, pp. 1637-1642 Barbieri, C., Bossi, L., D'Arrigo, P., Fantoni, G.P., Servi, S., Bioreduction of aromatic ketones: Preparation of chiral benzyl alcohols in both enantiomeric forms (2000) J. Mol. Catal. B: Enzym., 11, pp. 415-421 Brenelli, E.C.S., Carvalho, M., Okubo, M.T., Marques, M., Moran, P.J.S., Rodrigues, J.A.R., Sorrilha, E.P.M., Enantioselective synthesis of (R)-(-)-1-phenylethanolamines using Baker's yeast reduction of some a-substituted methyl phenyl ketones (1992) Indian J. Chem., 31 B, pp. 821-823 Carvalho, M., Okamoto, M.T., Moran, P.J.S., Rodrigues, J.A.R., Baker's yeast reduction of w-haloacetophenones (1991) Tetrahedron, 47, pp. 2073-2080 Corey, E.J., Link, J.O., The first enantioselective syntheses of pure R- and S-isoproterenol (1990) Tetrahedron Lett., 31, pp. 601-604 Cromwell, N.H., a,b-unsaturated amino-ketones. III. a- and b-morpholinobenzalacetones (1940) J. Am. Chem. Soc., 62, pp. 3470-3473 Effenberger, F., Hörsch, B., Ziegler, T., Ein einfacher zugang zu (R)-α-hydroxycar-bonsäuren und (R)-1-amino-2-alkoholen aus (R)-cyanhydrinen (1990) Synthesis, 7, pp. 575-578 Fardelone, L.C., Moran, P.J.S., Rodrigues, J.A.R., Bioreduction of a-substituted methyl aryl ketones mediated by Rhodotorula glutinis CCT 2182 and Geotrichum candidum CCT 1205 (2003) Arkivoc X, pp. 404-410 Gringauz, A., (1997) Introduction to Medicinal Chemistry: How Drugs Act and Why, p. 46. , Wiley-VCH, New York Hassner, A., L'Abbé, G., Miller, M.J., On the synthesis of a-azidovinyl ketones. Mechanism and stereochemistry of vinyl bromide substitution (1971) J. Am. Chem. Soc., 93, pp. 981-985 Hayashi, T., Katsumura, A., Konishi, M., Kumada, M., Asymmetric synthesis of 2-amino-1-arylethanols by catalytic asymmetric hydrogenation (1979) Tetrahedron Lett., 20, pp. 425-428 Kaufman, P.R., Wyman, D.P., The chlorination of active hydrogen compounds with sulfuryl chloride (1964) J. Org. Chem., 29, pp. 1956-1960 Kirk, K.L., (2000) Biomedical Chemistry Applying Chemical Principles to the Understanding and Treatment of Disease, p. 253. , Torrence P. F., Ed. Fluorine Substitution as a Modulator of Biological Processes. New York: Wiley-Interscience Ohta, H., Miyamae, Y., Tsuchihashi, G., Microbial hydrolysis of substituted mandelonitrile acetates and its application to the synthesis of optically active physiological ethanolamines (1989) Agric. Biol. Chem., 53, pp. 281-283 Sih, C., Chen, C.-S., Microbial asymmetric catalysis - Enantioselective reduction of ketones (1984) Ang. Chem., In. Ed. Eng., 23, pp. 570-578 Singer, R.A., Carreira, E.M., In situ procedure for catalytic enantioselective acetate aldol addition. Application to the synthesis of (R)-(-)-epinephrine (1997) Tetrahedron Lett., 38, pp. 927-930 Wendhausen Jr., R., Moran, P.J.S., Joekes, I., Rodrigues, J.A.R., Continuous process for the large-scale preparation of chiral alcohols with baker yeast immobilized on chrysotile fibers (1998) J. Mol. Catal. B: Enzym., 5, pp. 69-73