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 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.
Yamazaki
Takashi
T
Center of Future Nanomaterials, Institute of Symbiotic Sciences and Technology, Tokyo University of Agriculture and Technology, 2-24-16, Nakamachi, Koganei 184-8588, Japan. tyamazak@cc.tuat.ac.jp
Kobayashi
Rei
R
Kitazume
Tomoya
T
Kubota
Toshio
T
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
C516396:3,3,3-trifluoropropanal; D000447:Aldehydes; D006845:Hydrocarbons, Fluorinated; D002244:Carbon