Chiral crown ethers incorporating D-glucose

A novel class of crown ether derivatives incorporating D-glucose and poly(ethylene glycol) units has been synthesized from allyl α-D-glucopyranoside by a simple and efficient strategy. The complexing properties of these compounds with alkali metal cations and ammonium ion have been evaluated by Cram's picrate method. Catalytic activity of macrocycle 2 in asymmetric Michael addition reaction was also studied. The average cavity size of these macrocycles was determined by the application of the MMX programme