79416-50-5

Upstream product

• 58879-44-0 1-acetoxy-1-phenylbut-2-yne 
• 108-05-4 vinyl acetate 
• 32398-66-6 1-phenylbut-2-yn-1-ol 
• 100-52-7 benzaldehyde 
• 6710-62-9 1-phenyl-2-butyn-1-one 

Downstream Products

• 53544-89-1 (S)-buta-1,2-diene-1,3-diyldibenzene 

Relevant academic research and scientific papers

Laccase-mediated Oxidations of Propargylic Alcohols. Application in the Deracemization of 1-arylprop-2-yn-1-ols in Combination with Alcohol Dehydrogenases

The catalytic system composed by the laccase from Trametes versicolor and the oxy-radical TEMPO has been successfully applied in the sustainable oxidation of fourteen propargylic alcohols. The corresponding propargylic ketones were obtained in most cases in quantitative conversions (87–>99 % yield), demonstrating the efficiency of the chemoenzymatic methodology in comparison with traditional chemical oxidants, which usually lead to problems associated with the formation of by-products. Also, the stereoselective reduction of propargylic ketones was studied using alcohol dehydrogenases such as the one from Ralstonia species overexpressed in E. coli or the commercially available evo-1.1.200, allowing the access to both alcohol enantiomers mostly with complete conversions and variable selectivities depending on the aromatic pattern substitution (97–>99 % ee). To demonstrate the compatibility of the laccase-mediated oxidation and the alcohol dehydrogenase-catalyzed bioreduction, a deracemization strategy starting from the racemic compounds was developed through a sequential one-pot two-step process, obtaining a selection of (S)- or (R)-1-arylprop-2-yn-1-ols with excellent yields (>98 %) and selectivities (>98 % ee) depending on the alcohol dehydrogenase employed.

Kinetic resolution of propargylic alcohols via stereoselective acylation catalyzed by lipase PS-30

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic propargylic alcohols has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 139. Substituent effect is briefly discussed.

MICROBIALLY MEDIATED ENANTIOSELECTIVE HYDROLYSIS OF RACEMIC ACETATES

The enantioselective hydrolyses of a series of racemic hydroaromatic acetates by Rhizopus nigricans to produce optically active alcohols are described.A rule predicting the absolute stereochemistry of the resulting alcohols is proposed.