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. 2011:2011:976368.
doi: 10.4061/2011/976368. Epub 2011 Jun 2.

Chiral Pharmaceutical Intermediaries Obtained by Reduction of 2-Halo-1-(4-substituted phenyl)-ethanones Mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182

Lucídio C Fardelone  1 , J Augusto R Rodrigues, Paulo J S Moran
Affiliations

Chiral Pharmaceutical Intermediaries Obtained by Reduction of 2-Halo-1-(4-substituted phenyl)-ethanones Mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182

Lucídio C Fardelone et al. Enzyme Res. 2011.

Abstract

Enantioselective reductions of p-R(1)-C(6)H(4)C(O)CH(2)R(2) (R(1) = Cl, Br, CH(3), OCH(3), NO(2) and R(2) = Br, Cl) mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182 afforded the corresponding halohydrins with complementary R and S configurations, respectively, in excellent yield and enantiomeric excesses. The obtained (R)- or (S)-halohydrins are important building blocks in chemical and pharmaceutical industries.

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Figures

Scheme 1
Scheme 1
(a) reduction using chiral catalytic reagent or biocatalytic process; (b) base; (c) amine.
Scheme 2
Scheme 2
Figure 1
Figure 1
Prelog rule for discrimination of the faces of carbonylic group by the enzymes.
Figure 2
Figure 2
Pharmaceutical useful ethanolamines.
See this image and copyright information in PMC

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References

    1. Brenelli ECS, Carvalho M, Okubo MT, et al. Enantioselective synthesis of (R)-(-)-1-phenylethanolamines using Baker’s yeast reduction of some α-substituted methyl phenyl ketones. Indian Journal of Chemistry B. 1992;31:821–823.
    1. Barbieri C, Bossi L, D’Arrigo P, Fantoni GP, Servi S. Bioreduction of aromatic ketones: preparation of chiral benzyl alcohols in both enantiomeric forms. Journal of Molecular Catalysis B. 2001;11(4–6):415–421.
    1. Patel RN. Biocatalysis: synthesis of chiral intermediates for drugs. Current Opinion in Drug Discovery and Development. 2006;9(6):741–764. - PubMed
    1. Breuer M, Ditrich K, Habicher T, et al. Industrial methods for the production of optically active intermediates. Angewandte Chemie International Edition. 2004;43(7):788–824. - PubMed
    1. De Carvalho M, Okamoto MT, Moran PJS, Rodrigues JAR. Baker’s yeast reduction of α-haloacetophenones. Tetrahedron. 1991;47(12-13):2073–2080.

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