The diastero- and enantioselectivity of the presented reactions
is in agreement with the literature, where an anti-selective process
is the most common.14,15 However, a number of syn-selective
direct asymmetric aldol additions have also been reported.4,16
The application of Lewis acidic metal complexes (mimicking the
mode of action of type II aldolases) in solvents containing water
is still difficult.17 Zinc can act as an efficient Lewis acid, even in
the presence of water,18,19 so we assumed that our ligands in combination
with Zn(II) can create zinc-containing catalysts, which act
through the generation of a zinc enolate, as similarly described in
the literature.4,14–20 It should be mentioned that our ligands contain,
with the exception of an aziridinyl nitrogen atom which
should primarily coordinate a metal atom (strong effective complexation
of a zinc cation was described earlier21–23), five other
potential chelating centers. The proposal of any tentative mechanistic
model which could explain the interactions between the
substrate and catalysts seems to be rather premature and speculative
at this stage of our studies