Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/68970
Type: Artigo de periódico
Title: Hydride transfer versus electron transfer in the reduction of 4-phenyl-3-halo-3-buten-2-ones mediated by Pichia stipitis
Author: Zampieri, DS
Zampieri, LA
Rodrigues, JAR
de Paula, BRS
Moran, PJS
Abstract: Reductions of (Z)-C(6)H(5)CH=CXC(=O)CH(3) (X = Cl, Br) mediated by Pichia stipitis gave 4-phenylbutan-2-one through dehalogenation of intermediaries 3-halo-4-phenylbutan-2-one by an electron transfer mechanism. The addition of 1,3-dinitrobenzene avoids the dehalogenation and thus the corresponding (2S,3S)-halohydrins were obtained in excellent enantiomeric excesses by a hydride transfer mechanism. Irganox (R) 1010 and 1076 were also used to inhibit the electron transfer mechanism. The obtained halohydrins are important chiral building blocks to obtain optically active epoxides and aminoalcohols. (C) 2011 Elsevier B.V. All rights reserved.
Subject: Haloenones
Halohydrins
alpha-Haloketones
Enantioselective bioreduction
Pichia stipitis
Electron transfer mechanism
Country: Holanda
Editor: Elsevier Science Bv
Rights: fechado
Identifier DOI: 10.1016/j.molcatb.2011.07.001
Date Issue: 2011
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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