LIQUID-CHROMATOGRAPHIC ANALYSIS AND ISOLATION OF DIASTEREOISOMERS OBTAINED BY AN ALDOLIZATION REACTION

A new route using an aldolization reaction has been investigated in or der to synthesize a precursor of pilocarpin, an alkaloid having sympat homimetic properties. To study the stereoselectivity of this route and to propose a mechanism, liquid chromatography has been used to analys e and to isolate each diastereoisomer for a structural determination b y NMR. To further investigate the reaction mechanism, seven different aldehydes (or ketones) were used in the aldolization reaction, produci ng seven different mixtures. This paper describes the improvement of L C conditions with diol- and amino-bonded silica and the nonaqueous mob ile phases required for the isolation of each isomer.