A variety of optically active macrocyclic crown ethers that serve as "host" systems that are capable of differentiating between enantiomeric "guest" molecules during host-guest complexation have been prepared via incorporation of chiral elements into the crown ring skeleton. The ability of these crown ethers to recognize the enantiomers of guest salts, i.e., (+) a-methyl benzylamine and to transport them enantioselectively in W-tube transport experiments were studied. The ability of these crown ethers to perform as chiral catalysts in an enantioselective Michael addition was studied. The extent of asymmetric induction, expressed in terms of the enantiomeric excess (%ee), was monitored by measuring the optical rotation of the product and comparing to the literature value.