PREPARATION OF NEW CHIRAL QUATERNARY AMMONIUM-SALTS AND THEIR EVALUATION AS ENANTIOSELECTIVE PHASE-TRANSFER CATALYSTS

New optically active ammonium salts 4a, b, 5-8, 9a-d, 10, 12, and 13 are described. These are tested as enantioselective catalysts in six phase transfer catalysis reactions: peroxidation, N-alkylation, C-alkylation, borohydride reduction, epoxide formation, and Michael-like addition. Generally low enantiomeric excesses are observed. An interesting effect is found, however, with catalysts 12 and 13 where the stereochemistry of a remote center in the side chain exerts an remarkable effect.