141195-88-2Relevant 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.
AN EFFICIENT PREPARATION OF OPTICALLY ACTIVE (E)-γ-HYDROXY-α,β-UNSATURATED PHENYL SULFONES USING LIPASE-MEDIATED ACYLATIONS
Dominguez, Esteban,Carretero, Juan Carlos,Fernandez-Mayoralas, Alfonso,Conde, Santiago
, p. 5159 - 5162 (2007/10/02)
(E)-γ-Hydroxy-α,β-unsaturated phenyl sulfones have been efficiently resolved via irreversible enzymatic acylation with Lipase PS (Pseudomonas cepacia) and vinyl acetate.This process has been applied to the synthesis of the aggregation pheromone (-)-(3S,4S)-4-methyl-3-heptanol.
