Stereoselective synthesis of α-difluoromethyl-β-amino alcohols via nucleophilic difluoromethylation with Me3SiCF2SO2Ph

A facile synthesis of anti-α-(difluoromethyl)-β-amino alcohols was accomplished by using a nucleophilic difluoromethylation strategy with Me3SiCF2SO2Ph reagent. Good to excellent chemical yields as well as modest to good diastereoselectivity were achieved in these reactions. We found that the solvent played a crucial role in controlling the diastereoselectivity of the reaction, and an apolar solvent such as toluene helps to improve the diastereoselectivity of the reaction. The anti-α-(difluoromethyl)-β-amino alcohol 3a was demonstrated to be a useful synthetic intermediate to synthesize difluoromethylated oxazolidinone 9.