78303-40-9Relevant academic research and scientific papers
REACTION OF ALLYLSILANE WITH α-NITRO OLEFIN AND ITS DEVELOPMENT TO SYNTHESIS OF CYCLOPENTENONE
Ochiai, Masahito,,Arimoto, Masao,Fujita, Eiichi
, p. 1115 - 1118 (1981)
Michael addition of allylsilane to α-nitro olefin in the presence of AlCl3 proceeded smoothly at low temperature to give unsaturated nitronic acid, which was converted into the γδ-enone using aqueous Ti (III).Transformation of the enone into the 1,4-diketone followed by the intramolecular aldol condensation with the latter provided a convenient new synthesis of cyclopentanone.
Baeyer-Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters
Rodriguez, Cristina,Gonzalo, Gonzalo de,Torres Pazmino, Daniel E.,Fraaije, Marco W.,Gotor, Vicente
experimental part, p. 1168 - 1173 (2009/10/02)
The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic α-alkyl benzylketones with longer alkyl chains as well as with two substituted α-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis.
