132016-59-2

Upstream product

• 108-05-4 vinyl acetate 
• 129083-21-2 (E)-4-methyl-1-(phenylsulfonyl)pent-1-en-3-ol 
• 129083-18-7 (+/-)-(phenylsulfonyl)(p-tolylsulfinyl)methane 
• 590-86-3 isovaleraldehyde 
• 71398-23-7 (+)-(S)-4-Methylphenylsulfinyl phenyl sulfone 
• 56069-39-7 diethyl phenylsulfonylmethylphosphonate 

Downstream Products

• 147235-42-5 ((E)-(S)-3-Methoxymethoxy-4-methyl-pent-1-ene-1-sulfonyl)-benzene 
• 167358-38-5 (S)-1-((2S,3S)-3-Benzenesulfonyl-oxiranyl)-2-methyl-propan-1-ol 
• 167358-39-6 (S)-1-((2R,3R)-3-Benzenesulfonyl-oxiranyl)-2-methyl-propan-1-ol 
• 147332-03-4 (1E,3R,4S,5S)-5-(methoxymethoxy)-4,6-dimethyl-1-(phenylsulfonyl)-1-hepten-3-ol 
• 147235-51-6 (1E,3R,4S,5S)-5-(methoxymethoxy)-4,6-dimethyl-1-(trimethylsilyl)-1-(phenylsulfonyl)-1-hepten-3-ol 
• 1026318-55-7 ((2R,3S)-1-Benzenesulfonyl-3-methoxymethoxy-2,4-dimethyl-pentyl)-trimethyl-silane 
• 147235-49-2 (E)-(4R,5S)-1-Benzenesulfonyl-5-methoxymethoxy-4,6-dimethyl-hept-1-en-3-one 
• 147332-01-2 (2R,3S)-3-(methoxymethoxy)-2,4-dimethyl-1-(phenylsulfonyl)pentane 
• 147235-50-5 (1E,4R,5S)-5-hydroxy-4,6-dimethyl-1-(phenylsulfonyl)-1-hepten-3-one 

Relevant academic research and scientific papers

Aminooxylation Horner-Wadsworth-Emmons Sequence for the Synthesis of Enantioenriched γ-Functionalized Vinyl Sulfones

An operationally simple protocol for the synthesis of γ-hydroxy vinyl sulfones has been developed using a proline-based aldehyde aminooxylation, followed by a vinyl sulfone forming Horner-Wadsworth-Emmons olefination. The adducts, formed in high enantiopurity, were subsequently converted to γ-azido vinyl sulfones, and azide-alkyne click chemistry enabled the synthesis of vinyl sulfone-based triazoles as potential nonpeptidic cysteine protease inhibitors. (Chemical Equation Presented).

Lipase-Catalyzed Kinetic Resolution of γ-Hydroxy Phenyl Sulfones

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

(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.