FeCl3·6H2O-catalyzed mukaiyama-aldol type reactions of enolizable aldehydes and acetals

Alejandra Rodríguez-Gimeno, Ana B. Cuenca, Jesús Gil-Tomás, Mercedes Medio-Simón, Andrea Olmos, Gregorio Asensio

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17 Cites (Scopus)


Mukaiyama-aldol type reactions of acetals derived from enolizable aldehydes with FeCl3·6H2O, an eco-friendly, low-cost, and stable catalyst, lead to β-methoxycarbonyl compounds with nearly quantitative yields. The methodology is extended to the parent aldehydes as starting materials, leading to the corresponding aldols with lower yields, but efficiently. Different alkyl and aryl substituted acetals and aldehydes have been tested in the reaction with linear and cyclic silyl enol ethers. Reactions are carried out in an open air atmosphere, and additives are not required. Acetals can be considered activating groups of the carbonyl moiety rather than a protecting group in this type of FeCl3·6H2O-catalyzed condensation.

Idioma originalAnglès
Pàgines (de-a)8263-8270
Nombre de pàgines8
RevistaJournal of Organic Chemistry
Estat de la publicacióPublicada - 5 de set. 2014
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