III International Conference

PP-I-20NANOSIZED METAL OXIDES AS STEREOSELECTIVE CATALYSTS OF THEHANTZSCH AND BIGINELLI REACTIONSFedorova O., Ovchinnikova I., Kharchuk V., Rusinov G., Uimin M. 1 , Mysik A. 1 ,Ermakov A. 1 , Rhee C.K. 2 , Charushin V.Institute of Organic Synthesis RAS, Urals Branch, Ekaterinburg, Russia1 Institute of Metal Physics RAS, Urals Branch, Russia2 Korea Atomic Energy Research Institute (KAERI), Nuclear Materials TechnologyDevelopment Team, Yuseong, Daejeon, KoreaE-mail: rusinov@ios.uran.ruA new approach based on the nanosized metal oxides as catalysts has been used to obtaindihydropyrimidines and dihydropyridines. Metal oxide nanopowders were produced by gascondensation method (CuO and Al 2 O 3 ) and by hydrothermal treatment of Al nanopowder(AlOOH and Al 2 O 3 ). It has been shown that modification of a surface of nanosized metaloxides with chiral molecules effects on stereoselectivity of multicomponent reactions.For the first time nanosized metal oxides (Сu or Al) modified with chiral compoundshave been used as stereoselective catalysts of the multicomponent Biginelli and Hantzschreactions. It was revealed that in the presence of Al nanooxide the first stage of Hantzschreaction (the coupling of acetoacetic ether with aromatic aldehyde) results mainly in one oftwo possible isomers (Scheme 1, Figure 1).EtO 2COR+ RCOHCO 2Et+ROCO 2EtAl 2O 3Scheme 1Ocis-isomer trans-isomer80% 20%Figure 1. The structure of cis-isomer of Hantzsch reactionintermediate44