Microbial reduction with baker's yeast or Apergillus niger of methyl 4-chloro-4,4-difluoro-3-oxobutanoate afforded the optically active (-) methyl 4-chloro-4,4-difluoro-3-hydroxybutanoate. When the yeast reduction was carried out in the presence of allyl bromide the optically active (+) hydroxyester was obtained. Treatment of the (-)enantiomer with methylamine afforded the corresponding solid amide having (S) absolute configuration, as displayed by single crystal X-ray diffraction analysis.
Microbial Synthesis and Absolute Configuration of Methyl (+) and (-) 4-Chloro-4,4-difluoro-3-hydroxybutanoate / Antolini, Luciano; Forni, Arrigo; Moretti, Irene; Prati, Fabio; Torre, Giovanni. - In: GAZZETTA CHIMICA ITALIANA. - ISSN 0016-5603. - STAMPA. - 125:(1995), pp. 549-553.
Microbial Synthesis and Absolute Configuration of Methyl (+) and (-) 4-Chloro-4,4-difluoro-3-hydroxybutanoate.
ANTOLINI, Luciano;FORNI, Arrigo;MORETTI, Irene;PRATI, Fabio;TORRE, Giovanni
1995
Abstract
Microbial reduction with baker's yeast or Apergillus niger of methyl 4-chloro-4,4-difluoro-3-oxobutanoate afforded the optically active (-) methyl 4-chloro-4,4-difluoro-3-hydroxybutanoate. When the yeast reduction was carried out in the presence of allyl bromide the optically active (+) hydroxyester was obtained. Treatment of the (-)enantiomer with methylamine afforded the corresponding solid amide having (S) absolute configuration, as displayed by single crystal X-ray diffraction analysis.
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