105183-84-4Relevant articles and documents
Enantioselective kinetic resolution of 3-phenyl-2-ketones using Baeyer-Villiger monooxygenases
Geitner, Kristian,Kirschner, Anett,Rehdorf, Jessica,Schmidt, Marlen,Mihovilovic, Marko D.,Bornscheuer, Uwe T.
, p. 892 - 895 (2007)
The enantioselective kinetic resolution of two 3-phenyl-2-ketones using four different Baeyer-Villiger monooxygenases (BVMO) expressed recombinantly in Escherichia coli was studied. The highest enantioselectivity (E = 82) was achieved for 3-phenyl-2-butanone using a BVMO originating from Pseudomonas fluorescens. A BVMO from Pseudomonas putida showed an opposite (R)-enantiopreference and E = 12.
Cyanocuprates convert carboxylic acids directly into ketones
Genna, Douglas T.,Posner, Gary H.
supporting information; experimental part, p. 5358 - 5361 (2011/12/15)
Carboxylic acids were converted directly in 56-99% yields into methyl, n-butyl, and isopropyl ketones using excess cyanocuprates R2CuLi 3 LiCN. A substrate with a stereocenter α to the carboxylic acid was converted into ketones with very little loss of enantiomeric purity. A variety of functional groups were tolerated including aryl bromides. This direct transformation of a carboxylic acid into ketone with minimal tertiary alcohol formation is proposed to involve a relatively stable copper ketal tetrahedral intermediate.
BVMO-catalysed dynamic kinetic resolution of racemic benzyl ketones in the presence of anion exchange resins
Rodriguez, Cristina,De Gonzalo, Gonzalo,Rioz-Martinez, Ana,Torres Pazmino, Daniel E.,Fraaije, Marco W.,Gotor, Vicente
experimental part, p. 1121 - 1125 (2010/06/20)
4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB was employed in the presence of a weak anion exchange resin to perform dynamic kinetic resolutions of racemic benzyl ketones with high conversions and good optical purities. Different parameters that affect to the efficiency of the enzymatic Baeyer-Villiger oxidation and racemisation were analyzed in order to optimize the activity and selectivity of the biocatalytic system. The Royal Society of Chemistry.
Enzymatic kinetic resolution of racemic ketones catalyzed by Baeyer-Villiger monooxygenases
Rodriguez, Cristina,de Gonzalo, Gonzalo,Fraaije, Marco W.,Gotor, Vicente
, p. 1338 - 1344 (2008/02/09)
A set of racemic cyclic and linear ketones, as well as 2-phenylpropionaldehyde, were tested as substrates in the enzymatic Baeyer-Villiger oxidation catalyzed by two Baeyer-Villiger monooxygenases: phenylacetone monooxygenase (PAMO) and 4-hydroxyacetophenone monooxygenase (HAPMO). Excellent enantioselectivites (E > 200) can be obtained in the kinetic resolution processes depending on the substrate structure and the reaction conditions. The parameters affecting the biocatalytic properties of these enzymes were also studied, in order to establish a deeper understanding of these novel biocatalysts.
Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones
Myers, Andrew G.,Yang, Bryant H.,Chen, Hou,McKinstry, Lydia,Kopecky, David J.,Gleason, James L.
, p. 6496 - 6511 (2007/10/03)
The use of pseudoephedrine as a practical chiral auxiliary for asymmetric synthesis is described in full. Both enantiomers of pseudoephedrine are inexpensive commodity chemicals and can be N-acylated in high yields to form tertiary amides. In the presence of lithium chloride, the enolates of the corresponding pseudoephedrine amides undergo highly diastereoselective alkylations with a wide range of alkyl halides to afford α-substituted products in high yields. These products can then be transformed in a single operation into highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones.
