Synthesis of new enantiopure dimethyl-substituted pyridino-18-crown-6 ethers containing a hydroxymethyl, a formyl, ora carboxyl group at position 4 of the pyridine ring for enantiomeric recognition studies

Abstract

An enantiomerically pure dimethyl-substituted pyridino-18-crown-6 ether containing a hydroxymethyl group at position 4 of the pyridine ring [(S,S )-1] has been prepared. This by Swern oxidation gave the formyl-substituted [( S,S)-2], then by further oxidation carboxy-substituted [(S,S)-3 ] pyridino-18-crown-6 ether derivatives. These enantiopure dimethyl-substituted pyridino-18-crown-6 ethers [( S,S )-1-(S,S )-3 ] are good candidates for enantiomeric recognition studies and also very useful precursors for enantioselective sensor and selector molecules with wide applications. © ARKAT-USA, Inc.