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Chem Asian J ; 10(12): 2701-7, 2015 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-26206587

RESUMEN

A direct, concise, and enantioselective synthesis of 2-substituted 4,4,4-trifluorobutane-1,3-diols based on the organocatalytic asymmetric direct aldol reaction of an ethyl hemiacetal of trifluoroacetaldehyde with various aldehydes was examined. A catalytic amount (30 mol %) of commercially available and inexpensive l-prolinamide is quite effective as an organocatalyst for the catalytic in situ generation of gaseous and unstable trifluoroacetaldehyde from its hemiacetal, and a successive asymmetric direct aldol reaction with various aldehydes in dichloromethane at 0 °C, followed by reduction with sodium borohydride, gives 2-substituted 4,4,4-trifluorobutane-1,3-diols in moderate to good yields (31-84%) with low diastereoselectivities and good to excellent enantioselectivities (64-97% ee).


Asunto(s)
Acetaldehído/análogos & derivados , Butileno Glicoles/química , Acetaldehído/química , Aldehídos/química , Borohidruros/química , Butileno Glicoles/síntesis química , Catálisis , Cetonas/química , Cloruro de Metileno/química , Oxidación-Reducción , Prolina/análogos & derivados , Prolina/química , Estereoisomerismo
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