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

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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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo052434o