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FeCl3·6H2O-Catalyzed Mukaiyama-Aldol Type Reactions of Enolizable Aldehydes and Acetals

Author:
Rodríguez-Gimeno, Alejandra, Cuenca, Ana B., Gil-Tomás, Jesús, Medio-Simón, Mercedes, Olmos, Andrea, Asensio, Gregorio
Source:
Journal of organic chemistry 2014 v.79 no.17 pp. 8263-8270
ISSN:
1520-6904
Subject:
additives, air, aldehydes, catalysts, chemical reactions, ferric chloride, moieties, organic chemistry, silyl enol ethers
Abstract:
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.
Agid:
5502667