- In situ generation of 3,3,3-trifluoropropanal and its use for carbon-carbon bond-forming reactions
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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
- Yamazaki, Takashi,Kobayashi, Rei,Kitazume, Tomoya,Kubota, Toshio
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p. 2499 - 2502
(2007/10/03)
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- Convenient preparation of 2-phenylethyl 3,3-difluoro-2-methylpropionate
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The slow inverse addition of an LDA solution at -78 °C to an ester of 2-(trifluoromethyl)acrylic acid enabled efficient dehydrofluorination. Hydrogenation of the resulting difluoromethylacrylate furnished the target ester of 3,3-difluoro-2-methylpropionic
- Yamazaki, Takashi,Ichige, Tatsuro,Kitazume, Tomoya
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p. 1479 - 1485
(2007/10/03)
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- Effect of allylic CH3-nFn groups (n = 1-3) on π-facial diastereoselection
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(equation presented) Michael addition of various enolates toward γ-CH3-nFn-α,β-unsaturated ketones (n = 1-3) was proven to smoothly furnish the 1,4-adducts with high si face selectivities which monotonously decreased by reduction in the number of fluorines. Although the Felkin-Anh model correctly anticipates the present stereochemical outcome only with E-acceptors, the hyperconjugative stabilization of transition states by electron donation from the allylic substituents (the Cieplak rule) successfully explains the π-facial preference of both acceptors at least in a qualitative level.
- Yamazaki, Takashi,Ichige, Tatsuro,Takei, Satoshi,Kawashita, Seiji,Kitazume, Tomoya,Kubota, Toshio
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p. 2915 - 2918
(2007/10/03)
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