252061-10-2Relevant articles and documents
In situ generation of 3,3,3-trifluoropropanal and its use for carbon-carbon bond-forming reactions
Yamazaki, Takashi,Kobayashi, Rei,Kitazume, Tomoya,Kubota, Toshio
, p. 2499 - 2502 (2007/10/03)
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
Effect of allylic CH3-nFn groups (n = 1-3) on π-facial diastereoselection
Yamazaki, Takashi,Ichige, Tatsuro,Takei, Satoshi,Kawashita, Seiji,Kitazume, Tomoya,Kubota, Toshio
, p. 2915 - 2918 (2007/10/03)
(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.
