The author of 《Enantioselective resolution of side-chain modified gem-difluorinated alcohols catalysed by Candida antarctica lipase B and monitored by capillary electrophoresis》 were Pomeisl, Karel; Lamatova, Nikola; Solinova, Veronika; Pohl, Radek; Brabcova, Jana; Kasicka, Vaclav; Krecmerova, Marcela. And the article was published in Bioorganic & Medicinal Chemistry in 2019. Electric Literature of C9H10O2 The author mentioned the following in the article:
An enzymic alternative to the chem. synthesis of chiral gem-difluorinated alcs. has been developed. The method is highly effective and stereoselective, feasible at laboratory temperature, avoiding the use of toxic heavy metal catalysts which is an important benefit in medicinal chem. including the synthesis of drugs and drug precursors. Candida antarctica lipases A and B were applied for the enantioselective resolution of side-chain modified gem-difluorinated alcs., (R)- and (S)-3-benzyloxy-1,1-difluoropropan-2-ols (1a and 1b), compounds serving as chiral building blocks in the synthesis of various bioactive mols. bearing a gem-difluorinated grouping. The catalytic activity of these lipases was investigated for the chiral acetylation of 1a and 1b in non-polar solvents using vinyl acetate as an acetyl donor. The dependence of the reaction course on various substrate and enzyme concentrations, reaction time, and temperature was monitored by chiral capillary electrophoresis (CE) using sulfobutyl ether β-cyclodextrin as a stereoselective additive of the aqueous background electrolyte. The application of CE, NMR, and MS methods has proved that the complex enzyme effect of Candida antarctica lipase B leads to the thermodynamically stable (S)-enantiomer 1b instead of the expected acetylated derivatives In contrast, the enantioselective acetylation of racemic alc. 1 was observed as a kinetically controlled process, where (R)-enantiomer 1a was formed as the main product. This process was followed by enzymic hydrolysis and chiral isomerization. Finally, single pure enantiomers 1a and 1b were isolated and their absolute configurations were assigned from NMR anal. after esterification with Mosher’s acids. In the experiment, the researchers used many compounds, for example, 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3Electric Literature of C9H10O2)
2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).Electric Literature of C9H10O2
Referemce:
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Ether | (C2H5)2O – PubChem