TY - JOUR
T1 - FeCl3·6H2O-catalyzed mukaiyama-aldol type reactions of enolizable aldehydes and acetals
AU - Rodríguez-Gimeno, Alejandra
AU - Cuenca, Ana B.
AU - Gil-Tomás, Jesús
AU - Medio-Simón, Mercedes
AU - Olmos, Andrea
AU - Asensio, Gregorio
N1 - Publisher Copyright:
© 2014 American Chemical Society.
PY - 2014/9/5
Y1 - 2014/9/5
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84924308112&partnerID=8YFLogxK
U2 - 10.1021/jo501498a
DO - 10.1021/jo501498a
M3 - Article
AN - SCOPUS:84924308112
SN - 0022-3263
VL - 79
SP - 8263
EP - 8270
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -