Jm. Andres et al., EASY PREPARATION OF ENANTIOPURE C-2-SYMMETRICAL AMINOALCOHOLS DERIVEDFROM M-XYLYLENE DIAMINE, Tetrahedron : asymmetry, 5(1), 1994, pp. 57-66
The title compounds were prepared by condensation of isophthaldehyde w
ith chiral amino alcohols or alpha-amino esters in three different way
s depending on the substitution pattern. These methods are: for N-subs
tituted amino alcohols, by reduction of the epimeric mixtures of 1,3-o
xazolidines formed in the condensation process; for unsubstituted ones
, by reduction of the corresponding hydroxy imines, followed by N-alky
lation; and for the imines obtained in the condensation with amino eat
ers, by sequential reduction and reaction with methylmagnesium iodide.