Synthesis of new enantiopure dimethyl and diisobutyl…新的对映异构体二甲基和二异丁基的合成.pdfVIP

General Papers ARKIVOC 2011 (ix) 77-93 Synthesis of new enantiopure dimethyl- and diisobutyl -substituted pyridino-18-crown-6 ethers containing a halogen atom or a methoxy group at position 4 of the pyridine ring for enantiomeric recognition studies József Kupai,a Péter Huszthy,a,b* Kata Székely,a Tünde Tóth,a,b and László Párkányic aDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, Hungary bResearch Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, H-1521 Budapest, Hungary cChemical Research Center, Institute of Structural Chemistry, X -ray Diffraction Laboratory of the Hungarian Academy of Sciences, H-1525 Budapest, P.O. Box. 17 E-mail: huszthy@mail.bme.hu Abstract New enantiomerically pure dimethyl- and diisobutyl-substituted pyridino-18-crown-6 ethers containing a halogen atom or a methoxy group at position 4 of the pyridine ring [(S,S)-1, (S,S)-2, (S,S)-3, (S,S)-4] have been synthesized. A new synthetic route and the solid state structure of the reported enantiopure dimethyl-substituted pyridino-18-crown-6 ether [(S,S)-5] containing a chlorine atom at position 4 of the pyridine ring are also described. These ligands are good candidates for enantiomeric recognition studies of protonated primary amines, amino acids and their derivatives. Keywords: Chiral crown ethers, pyridino-18-crown-6 ligands, macrocycles, heterocycles, enantiomeric recognition, chiral stationary phases Introduction There are numerous examples of molecular recognition