||(Z)-Selective enol triflation of α-alkoxyacetoaldehydes: Application to synthesis of (Z)-allylic alcohols via cross-coupling reaction and [1,2]-wittig rearrangement
Kurosawa, Fumiya ,
Nakano, Takeo ,
Soeta, Takahiro ,
Endo, KoheiUkaji, Yutaka
Journal of Organic Chemistry
5703 , 2015-06-05 , American Chemical Society
The stereoselective transformation of α-alkoxyacetoaldehydes to the corresponding (Z)-vinyl triflates was achieved by treatment with phenyl triflimide and DBU. The stereochemistry was explained by the "syn-effect," which was attributed primarily to an σ → π∗ interaction. The β-alkoxy vinyl triflates obtained were applied to the stereoselective synthesis of structurally diverse (Z)-allylic alcohols via transition metal-catalyzed cross-coupling reaction and [1,2]-Wittig rearrangement. © 2015 American Chemical Society.