1516-34-3Relevant articles and documents
Catalytic Asymmetric Synthesis of Quaternary Barbituric Acids
Del Pozo, Sandra,Vera, Silvia,Oiarbide, Mikel,Palomo, Claudio
supporting information, p. 15308 - 15311 (2017/11/06)
The catalytic asymmetric α-functionalization of prochiral barbituric acids, a subtype of pseudosymmetric 1,3-diamides, to yield the corresponding 5,5-disubstituted (quaternary) derivatives remains essentially unsolved. In this study 2-alkylthio-4,6-dioxopirimidines are designed as key 1,3-diamide surrogates that perform exceedingly in amine-squaramide catalyzed C-C bond forming reactions with vinyl ketones or Morita-Baylis-Hillmann-type allyl bromides as electrophiles. Mild acid hydrolysis of adducts affords barbituric acid derivatives with an in-ring quaternary carbon in unprecedented enantioselectivity, offering valuable materials for biological evaluations.