Enantioselective Aldol Reaction with Difluoroenoxysilanes Catalyzed by Cationic Palladium Aqua Complexes

The enantioselective addition of difluoroenoxysilanes to aromatic aldehydes, catalyzed by cationic palladium aqua complexes, has been described. The reaction is operationally simple, does not require anhydrous conditions and performs at room temperature. The palladium catalysts, previously discovered and reported by Sodeoka, are easily prepared in two steps from PdCl2(MeCN)(2). The aldol compounds were obtained in good yields and with enantiomeric ratios up to 93 : 7, the reaction being more efficient using electron-rich aldehydes.

Automated summary

The enantioselective addition of difluoroenoxysilanes to aromatic aldehydes, catalyzed by cationic palladium aqua complexes, was achieved. The reaction is easy to carry out, does not require anhydrous conditions, and can be performed at room temperature. The palladium catalysts, previously discovered and reported by Sodeoka, can be prepared in two steps from PdCl2(MeCN)(2). The aldol compounds were obtained in good yields and with enantiomeric ratios up to 93 : 7, with higher efficiency observed using electron-rich aldehydes.