54827-32-6

Upstream product

• 174858-25-4 methyl (2Z)-2-(chloromethyl)-3-phenylprop-2-enoate 
• 100-52-7 benzaldehyde 
• 18020-59-2 methyl 3-hydroxy-2-methylidene-3-phenylpropionate 
• 54827-25-7 2-Diethoxymethyl-1-phenyl-prop-2-en-1-ol 
• 54827-29-1 3-phenyl-3-hydroxy-2-methylenepropanal 

Downstream Products

• 7384-80-7 (S)-2-methyl-3-phenylpropan-1-ol 
• 77943-96-5 (2R)-2-methyl-3-phenyl-1-propanol 

Relevant academic research and scientific papers

On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering

The Baker's Yeast (BY) reduction of (Z)-2-chloromethyl-3-arylacrylaldehydes was found to afford (R)-2-methyl-3-aryl-propanols showing high enantiomeric excess values. Deuterium incorporation experiments were performed, in order to investigate the mechanism of the bioreduction: the formation of the corresponding substituted 2-benzylacrylaldehydes, as intermediates to be effectively reduced by Baker's Yeast, was suggested. These intermediates were synthesized and submitted to BY reduction to afford the corresponding saturated (R)-alcohols, thus confirming the conclusions drawn from labelling experiments. The enantioselectivity of their bioreduction was found to be opposite with respect to that observed for the corresponding regioisomeric 2-methylcinnamaldehydes. The preparation of the two enantiomers of 2-methyl-3-aryl-propanols by fermentation of two regioisomers represents an interesting example of substrate-controlled enantioselective reaction.

Aldolisation dirigee avec l'acroleine. Methode de synthese stereoselective de doubles liaisons trisubstituees fonctionnalisees. Application a la synthese du (+/-)-Z-chloronuciferal et du (+/-)-E-nuciferol

To direct the aldolisation reaction in such a way that an aldehyde reacts upon the electrophilic carbonyl group of a ketone or of another aldehyde, it is necessary to mask the aldehyde and to transform it into a nucleophile.The present article presents an approach to this problem concerning unsaturated aldehydes and describes the condensation between the α-carbanion of acrolein and several carbonyl compounds. Aldol condensation at -70 degC, between 1,1-diethoxy-2-lithio-2-propene and several aldehydes leads to β-hydroxy-α-methylene acetals.These secondary allylic alcohols are stereoselectively transformed into trisubstituted functionalised olefinic compounds (Z-α-chlormethyl-α,β-unsaturated aldehydes and E-α-methyl-α,β-unsaturated primary alcohols). This method is illustrated by the syntheses of (+/-)-Z-chloronuciferal and (+/-)-E-nuciferol.