The DIBAL reduction of 2-phenylethyl 3,3,3-trifluoro-2-methylpropionate 2 at -78 degrees C afforded the aluminum acetal 3, and this intermediate, on worming up to 0 degrees C, was found to slowly decompose into the corresponding aldehyde 4, which smoothly reacted with appropriate nucleophiles in a one-pot manner in good to excellent yields with up to 93% diastereoselectivity.

Aldehydes P 0170In situ Generation of 3,3,3-Trifluoropropanal and Its Use for Carbon-Carbon Bond-Forming Reactions. -Treatment of the ester (I) with DIBAL results in formation of the title aldehydes: it is unstable and cannot be isolated. However, it can be trapped with diverse nucleophiles as an easy access to halogenated alcohols of type (III),(V), and (VII). -(YAMAZAKI*, T.; KOBAYASHI, R.; KITAZUME, T.; KUBOTA, T.; J.