Indium-promoted chemo- and diastereoselective allylation of α,ß-epoxy ketones with potassium allyltrifluoroborate.

A practical method for the chemo- and diastereoselective allylation of α,ß-epoxy ketones has been developed by using the convenient air and moisture stable reagent potassium allyltrifluoroborate. Indium metal was found to promote addition in stoichiometric or catalytic amounts, to afford α,ß-epoxyhomoallylic tertiary alcohols in high yields and diastereoselectivities, without competing ring-scission of the epoxide.

Allylation and crotylation of ketones and aldehydes using potassium organotrifluoroborate salts under Lewis acid and montmorillonite K10 catalyzed conditions.

Two convenient highly diastereoselective protocols for the allylation and crotylation of ketones using practical, air- and water-stable potassium allyl and crotyltrifluoroborate salts have been developed. BF(3).OEt(2) and montmorillonite clay are used as catalysts to promote additions. The montmorillonite-catalyzed method in particular is very robust, providing a straightforward and scalable method for the allylation and crotylation of a range of ketones and aldehydes.

The facile and efficient Michael addition of indoles and pyrrole to alpha,beta-unsaturated electron-deficient compounds catalyzed by aluminium dodecyl sulfate trihydrate [Al(DS)3].3H2O in water.

Aluminium dodecyl sulfate trihydrate [Al(DS)3].3H2O is easily prepared and can be used as a Lewis acid surfactant catalyst in water to conduct the highly efficient Michael addition of indoles and pyrrole to alpha,beta-unsaturated electron-deficient compounds at room temperature.

Aluminium dodecatungstophosphate (AlPW12O40) as a highly efficient catalyst for the selective acetylation of -OH, -SH and -NH2 functional groups in the absence of solvent at room temperature.

AlPW12O40 was found to be an effective catalyst for the selective acetylation of alcohols, thiols, and amines in the absence of solvent at room temperature.