Combining chiral elements in asymmetric phase-transfer catalysts: styrene oxide and chiral α,α-disubstituted pyrroline and piperidine derived structures

A new asymmetric phase-transfer catalyst, designed by combining the chiral building blocks styrene oxide and 2,5-dimethylpyrroline, is described. Catalytic testing using standard glycine imino ester alkylations shows good yields and moderate to good enantioselectivities with a surprising change in enantioselectivity over the course of the reaction. Alkylation of the β-hydroxyl group lead to catalysts with improved selectivity and a larger change in enantioselectivity during the reaction.