Study on the synthesis of chiral 1,2-amino alcohols

Abstract

The novel synthetic routes for chiral 1,2-amino alcohols have been developed from α -amidoalkylphenyl sulfones and various N-sulfinimines. α -amidoalkylphenyl sulfones were reacted with benzyloxymethyllithium to give fully protected amino alcohols with high yields. Chiral 1,2 amino alcohols were synthesized by addition of [(dimethyphenylsilyl)methyl] magnesium chloride to chiral sulfinimine, followed by silyl oxidation and transformation of approprite funtional group. When the reactions were carried out at room temperature in THF with 2 equivalent of [(dimethylphenylsilyl)methyl] magnesium chloride, high diastereoselectivity was observed (up to 98% d.e.).