54827-25-7

Upstream product

• 17592-40-4 2-bromo-3,3-diethoxypropene 
• 100-52-7 benzaldehyde 

Downstream Products

• 54827-29-1 3-phenyl-3-hydroxy-2-methylenepropanal 
• 98698-53-4 2-Diethoxymethyl-1-phenyl-propenone 
• 80322-06-1 3,3-Diethoxy-2-methyl-1-phenyl-propan-1-ol 
• 54827-32-6 (Z)-2-(chloromethyl)-3-phenylacrylaldehyde 

Relevant academic research and scientific papers

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.