Synthesis of a novel cage-functionalized chiral binaphthol host: a potential new agent for enantioselective recognition of chiral ammonium salts

Optically active, cage-functionalized crown ether (R)-3 which contains a 1, 1'-bi-2-naphthol moisty has been prepared. Subsequently, the ability of(R)- 3 to selectively recognize the enantiomers of guest ammonium salts, i.e., 4 and 5 in transport experiments was studied. Host (R)-3 displays significan tly enhanced enantiomeric selectivity toward complex formation with 4 vis-a -vis complex formation with 5. The relative energetics of various relevant host-guest complexes have been investigated computationally. (C) 2000 Elsev ier Science Ltd. All rights reserved.