22038-58-0Relevant articles and documents
Enoate reductase-mediated preparation of methyl (S)-2-bromobutanoate, a useful key intermediate for the synthesis of chiral active pharmaceutical ingredients
Brenna, Elisabetta,Gatti, Francesco G.,Manfredi, Alessia,Monti, Daniela,Parmeggiani, Fabio
experimental part, p. 262 - 268 (2012/06/18)
Enoate reductases belonging to the Old Yellow Enzyme (OYE) family were employed to develop a biocatalysed approach to methyl (S)-2-bromobutanoate, a key intermediate for the introduction of a particular stereogenic unit into the molecular skeleton of a certain class of chiral drugs. Methyl (Z)-2-bromocrotonate afforded, respectively, (S)-2-bromobutanoic acid (ee = 97%) and methyl (S)-2-bromobutanoate (ee = 97%) by baker's yeast fermentation and by OYE1-3 biotransformations. The bioreductions of other methyl 2-haloalkenoates were also considered. It was observed that the (Z)- and (E)-diastereoisomers of α-bromo unsaturated esters afforded the same enantiomer of the corresponding reduced product.
Stereoselective dehydrobromination of alkyl α-Br α-Cl-carboxylates
Forti, Luca
, p. 3023 - 3026 (2007/10/02)
(Z)-Alkyl α-Cl-α,β-unsaturated esters are prepared in excellent yields by stereoselective dehydrobromination of alkyl α-Br-α-Cl-carboxylates with LiCl-Li2CO3 in dimethylformamide.
A facile synthesis of optically pure L-armentomycin and its D-isomer. Highly enantioselective reduction of the C-C double bond of methyl (E)- and (Z)-2,4,4-trichloro-2-butenoate by using Baker's yeast
Utaka,Konishi,Okubo,et al.
, p. 1447 - 1450 (2007/10/02)
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