Searching for asymmetric inductions in chiral smectic mesophases

Abstract

Searching for asymmetric synthesis in smectic phases is, to our knowledge, reported for the first time in this paper. Two different reactions able to lead to optical enrichment were carried out in smectic phases (S) composed of chiral molecules. The first was a thermally promoted 1,3 dipolar cycloaddition of a diazo compound to a prochiral thiocarbonyl derivative run in a chiral smectic C meso-phase (S*_C). The second was a monomolecular process, the photochemical inversion of chiral sulphoxides in a smectic A mesophase. In both cases the asymmetric induction was zero or, in the best run, very very poor. This lack of transfer of chirality between the smectic solvent and the reaction is discussed to understand better the requirements for more successful tailoring of such experiments.