108644-06-0Relevant academic research and scientific papers
Lipase-Catalyzed Kinetic Resolution of γ-Hydroxy Phenyl Sulfones
Carretero, Juan C.,Dominguez, Esteban
, p. 3867 - 3873 (2007/10/02)
Lipase PS (from Pseudomonas cepacia) catalyzed the enantioselective transesterification of racemic γ-hydroxy-α,β-unsaturated phenyl sulfones 1 and their α,β-saturated derivatives 3 with vinyl acetate in an organic solvent (usually iPr2O).Remarkably, in substrates 1 with (E)-stereochemistry, the enantioselectivity of the process was little influenced by the nature of the R chain.Hence, very high enantiomeric ratios (E>/=45) were observed in substrates 1 bearing short (R = Me or Et), long (R = n-C6H13 or n-C10H21), bulky (R = iPr), or functionalized R chains.The (R)-enantiomer was the fast-reacting enantiomer in all cases.Concerning the reactivity, the rate of the reaction decreased significantly with an increase in size of length of the R chain (reaction time for 50percent conversion from 3.5 to 162 h).Less satisfactory enantioselectivities (E = 5-48) were obtained when the saturated substrates 3 were used instead of the corresponding α,β-unsaturated alcohols 1.
Preparation of Hydrindenones from 2-Methylcyclopent-2-enone and the Carbanion of (E)-But-2-enyldiphenylphosphine Oxide: Efficient Enolate Trapping with β-Sulphonylvinyl Ketones
Haynes, Richard K.,Vonwiller, Simone C.
, p. 92 - 94 (2007/10/02)
The β-sulphonylvinyl ketones (5), (7), (9), and (10), easily prepared from β-(phenylthio)propionyl chloride or from methyl vinyl ketone, react efficiently with the enolate produced by the conjugate addition of the carbanion of (E)-but-2-enyldiphenylphosph
