Synthesis of new bipyridine N,N′-dioxides and their application in asymmetric allylation of benzaldehyde and aldol addition to acetophenone

• DOI: 10.1007/s00706-018-2289-5
• Publication Date: 2018-11-13T05:45:55Z
• Authors: Eva Bednářová; David Nečas; Ivana Císařová; Michal Dušek; Frédéric Lamaty; Martin Kotora
• Keywords: [CHIM] Chemical Sciences; [CHIM]Chemical Sciences; 01 natural sciences; 3. Good health; 0104 chemical sciences

Two methods for the synthesis of new axially chiral bipyridine N,N′-dioxides based on catalytic [2+2+2] cyclotrimerization of diynes with nitriles were developed. The N,N′-dioxides were used as catalysts in enantioselective allylation of benzaldehyde with allyltrichlorosilane and aldol reaction of trichlorosilyl ketene acetal of methyl acetate with acetophenone.