The aim of this research project was to study chalcogen based organocatalysts in respect of their kinetic and enantioselective behavior in acylation reactions. Different nucleophilic oxygen species such as amino alcohols, sulfoxides and amino sulfoxides have been investigated how neighboring groups, steric and electronic effects influence the methanolysis of para-nitrophenyl ester of propionic acid. High catalytic activities could be achieved with β amino alcohol catalysts. Their mechanism of action could be determined as O-nucleophilic mechanism. The screening of various organocatalysts affords the basis for the optimization of the structure of the best catalysts, in order to use this one for the enantioselective anhydride-opening of cylic meso-anhydrides. The most efficient catalyst is the β-amino alcohol catalyst derived from isosorbide, a by-product from the starch industry. In addition to its good catalytic activity, this new catalyst promotes the enantioselective alcoholysis of various cyclic meso-anhydrides in high enantiomeric excess and quantitative yields. Based on the high catalytic effect of β-amino alcohol moiety, the regioselective acylation of Clarithromoycin and Tilmicosin, macrocycle antibiotics possessing an amino sugar moiety, is described.