In situ generation of 3, 3, 3-trifluoropropanal and its use for carbon-carbon bond-forming reactions

T Yamazaki, R Kobayashi, T Kitazume…

Index: Yamazaki, Takashi; Kobayashi, Rei; Kitazume, Tomoya; Kubota, Toshio Journal of Organic Chemistry, 2006 , vol. 71, # 6 p. 2499 - 2502

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Citation Number: 18

Abstract

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.