52883-79-1Relevant academic research and scientific papers
Chemoenzymatic Dynamic Kinetic Asymmetric Transformations of β-Hydroxyketones
Hilker, Simon,Posevins, Daniels,Unelius, C. Rikard,B?ckvall, Jan-E.
, p. 15623 - 15627 (2021/10/07)
Herein we report on the development and application of chemoenzymatic Dynamic Kinetic Asymmetric Transformation (DYKAT) of α-substituted β-hydroxyketones (β-HKs), using Candida antartica lipase B (CALB) as transesterification catalyst and a ruthenium complex as epimerization catalyst. An operationally simple protocol allows for an efficient preparation of highly enantiomerically enriched α-substituted β-oxoacetates. The products were obtained in yields up to 95 % with good diastereomeric ratios.
Synthesis of valuable chiral intermediates by isolated ketoreductases: Application in the synthesis of α-alkyl-β-hydroxy ketones and 1,3-diols
Kalaitzakis, Dimitris,Rozzell, J. David,Smonou, Ioulia,Kambourakis, Spiros
, p. 1958 - 1969 (2007/10/03)
Regio- and stereoselective reductions of α-substituted 1,3-diketones to the corresponding β-keto alcohols or 1,3-diols by using commercially available ketoreductases (KREDs) are described. A number of α-monoalkyl- or dialkyl-substituted symmetrical as well as non-symmetrical diketones were reduced in high optical purities and chemical yields, in one or two enzymatic reduction steps. In most cases, two or even three out of the four possible diastereomers of α-alkyl-β-keto alcohols were synthesized by using different enzymes, and in two examples both ketones were reduced to the 1,3-diol. By replacing the α-alkyl substituent with the OAc group, 1-keto-2,3-diols, as well as 1,2,3-triols were synthesized in high optical purities. These enzymatic reactions provide a simple, highly stereoselective and quantitative method for the synthesis of different diastereomers of valuable chiral synthons from non-chiral, easily accessible 1,3-diketones.
Highly stereoselective reductions of α-alkyl-1,3-diketones and α-alkyl-β-keto esters catalyzed by isolated NADPH-dependent ketoreductases
Kalaitzakis, Dimitris,David Rozzell,Kambourakis, Spiros,Smonou, Ioulia
, p. 4799 - 4801 (2007/10/03)
(Chemical Equation Presented) The biocatalytic reduction of α-alkyl-1,3-diketones and α-alkyl-β-keto esters employing 1 of 20 different isolated NADPH-dependent ketoreductases proved to be a highly efficient method for the preparation of optically pure keto alcohols or hydroxy esters.
