The reaction of cyclobutane-1,2-dione with hydroxide was studied by a variety of ab initio (MP2, SCS-MP2, CCSD(T), CEPA/1) and density functional (M06-2X) methods. Three possible reaction paths of the initially formed tetrahedral adduct leading to either 1-hydroxycyclopropane-1-carboxylate (benzilic acid type rearrangement, path A), α-oxobutanoate (path B) or γ-oxobutanoate (path C) were consid...

Novotný O., Cejpek K., Velíšek J. (2008): Formation of carboxylic acids during degradation of monosaccharides. Czech J. Food Sci., 26: 117–131. The formation of low molecular carboxylic and hydroxycarboxylic acids as well as sugar and deoxysugar acids from monosaccharides (d-glucose, d-fructose, d-arabinose, dl-glyceraldehyde, and 1,3-dihydroxyacetone) was studied in three different model syste...

The Hooker oxidation is one of the most intriguing transformations wherein lapachol (1) is readily converted to norlapachol (2) in very good yield. This one-pot reaction involves a very intricate mechanism in which the alkyl side chain of lapachol is shortened by one carbon unit. Previous studies have unequivocally established the involvement of an indane carboxylic acid derivative 3, as a key ...

An efficient two-step protocol for the asymmetric synthesis of 1H-pyrrol-3(2H)-one derivatives in 99% ee from conveniently accessed 2,3-diketoesters has been developed.