Chiral, non-racemic, distally-bridged resorcin[4]arenes as models for use in asymmetric processes

The synthesis of enantiomerically pure, distally-bridged resorcinarenes 3 w ith various R groups (CH3, C5H11, C-11 H-23) is reported. The key step make s use of the Mannich reaction for attachment of a chiral diamine-line 2 acr oss the cavity. Yields for this step are good to excellent. One of the brid ged compounds exhibits modest activity (27% ee) as an enantioselective cata lyst in the addition of diethylzinc to benzaldehyde.