In Situ Generation of 3,3,3-Trifluoropropanal and Its Use for Carbon−Carbon Bond-Forming Reactions

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

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Veröffentlicht in:	Journal of organic chemistry 2006-03, Vol.71 (6), p.2499-2502
Hauptverfasser:	Yamazaki, Takashi, Kobayashi, Rei, Kitazume, Tomoya, Kubota, Toshio
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemical synthesis Aldehydes - chemistry Carbon - chemistry Chemistry Exact sciences and technology Hydrocarbons, Fluorinated - chemical synthesis Hydrocarbons, Fluorinated - chemistry Molecular Conformation Organic chemistry Stereoisomerism
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description	The DIBAL reduction of 2-phenylethyl 3,3,3-trifluoro-2-methylpropionate 2 at −78 °C afforded the aluminum acetal 3, and this intermediate, on worming up to 0 °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.
doi_str_mv	10.1021/jo052434o
format	Article
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subjects	Aldehydes - chemical synthesis Aldehydes - chemistry Carbon - chemistry Chemistry Exact sciences and technology Hydrocarbons, Fluorinated - chemical synthesis Hydrocarbons, Fluorinated - chemistry Molecular Conformation Organic chemistry Stereoisomerism
title	In Situ Generation of 3,3,3-Trifluoropropanal and Its Use for Carbon−Carbon Bond-Forming Reactions
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