908299-83-2Relevant academic research and scientific papers
(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, Kohei,Ukaji, Yutaka
, p. 5696 - 5703 (2015/06/16)
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.
Direct, stereospecific generation of (Z)-disubstituted allylic alcohols
Jeon, Sang-Jin,Fisher, Ethan L.,Carroll, Patrick J.,Walsh, Patrick J.
, p. 9618 - 9619 (2007/10/03)
A one-pot method to prepare highly functionalized (Z)-disubstituted allylic alcohols is introduced. Hydroboration of a variety of 1-bromo-1-acetylenes with dicyclohexyl borane, reaction with t-BuLi, and transmetalation to zinc generates a (Z)-disubstituted vinylzinc reagent. In situ reaction of this reagent with aldehydes generates (Z)-disubstituted allylic alcohols in high yields (81-97%). Addition to chiral protected α- or β-oxygenated aldehydes proceeds with diastereoselectivities between 6:1 and 18:1. The anti-Felkin product is obtained in most cases. Copyright
