Easy preparation of enantiopure C 2-symmetrical aminoalcohols derived from m-xylylene diamine.

Abstract

The title compounds were prepared by condensation of isophthaldehyde with chiral amino alcohols or α-amino esters in three different ways depending on the substitution pattern. These methods are: for N-substituted amino alcohols, by reduction of the epimeric mixtures of 1,3-oxazolidines formed in the condensation process; for unsubstituted ones, by reduction of the corresponding hydroxy imines, followed by N-alkylation; and for the imines obtained in the condensation with amino esters, by sequential reduction and reaction with methylmagnesium iodide.