138002-05-8Relevant academic research and scientific papers
Lipase catalysed kinetic resolution of racemic 1,2-diols containing a chiral quaternary center
De Gonzalo, Gonzalo
, (2018/07/13)
Optically active 1,2-diols are valuable buildings blocks in organic synthesis. In the present paper, a set of racemic 1,2-diols with an ester functional group are prepared, starting from α-ketoesters in a three-step procedure with moderate yields. The racemic 1,2-diols, containing a chiral quaternary center in their structure, are subjected to selective acylation in order to perform their kinetic resolution catalysed by a set of commercially available lipases. Under optimized reaction conditions, good conversions and enantioselectivities are achieved by using the lipase PSL-C from Pseudomonas cepacia in tert-butyl methyl ether. This biocatalyst could be reused up to five times without losing its properties.
Dihydroxyacids from the chlorination of ketones: an unexpected process
Guthrie, J. Peter,Cossar, John,Lu, Jinqiao
, p. 1904 - 1908 (2007/10/02)
Chlorination of propiophenone in aqueous alkali at room temperature, with low concentrations of hypochlorite, leads to 2-phenylglyceric acid as the major product.This acid is formed by further oxidation of 1-phenyl-1,2-propanedione, which is an intermediate in the oxidation of propiophenone.Formation of this acid is reasonable in the light of other halogenation chemistry.Analogous reactions are observed for butyrophenone, which yields 2,3-dihydroxy-2-phenylbutanoic acid, and for cycloheptanone, which yields 1,2-dihydroxycyclohexanecarboxylic acid. Key words: 2-phenyl glyceric acid, propiophenone, chlorination, hydrolysis, rearrangement, cycloheptanone, 1,2-dihydroxycyclohexanecarboxylic acid.
