852913-16-7Relevant articles and documents
Access to Chiral Polycyclic 1,4-Dihydropyridines via Organocatalytic Formal [3 + 3] Annulation of 2-(1-Alkynyl)-2-alken-1-ones with 3-Aminobenzofurans
Li, Zhanhuan,Zhou, Hongwei,Xu, Jianfeng
, p. 6391 - 6395 (2021)
A rational designed tandem reaction of 2-(1-alkynyl)-2-alken-1-ones with 3-aminobenzofurans enabled by a chiral bifunctional catalyst is described, affording biologically significant polycyclic 1,4-dihydropyridines in moderate to good yields (43-82%) with good to excellent enantioselectivities (83-99%). This formal [3 + 3] annulation reaction reveals good practicality when conducted on a gram scale, and the cycloadduct has the capability for further elaborations.
Asymmetric Cycloetherification by Bifunctional Organocatalyst
Asano, Keisuke,Matsubara, Seijiro
, p. 4243 - 4253 (2018/07/03)
Attempts to obtain enantiomerically enriched tetrahydrofuran derivatives via an intramolecular oxy -Michael addition reaction of ?-hydroxyenone is discussed. Despite previous difficulties associated with the asymmetric induction of this reaction, which can proceed even without a catalyst, a highly efficient asymmetric induction was realized using a bifunctional organocatalyst derived from a cinchona alkaloid. The reaction could be extended to ζ-hydroxyenone to yield an optically active tetrahydropyran derivative with a high ee. In these reactions, it is important for the gentle acidic and basic sites in the bifunctional organocatalyst to be arranged properly within the molecular skeleton of the catalyst. The high performance asymmetric induction relied on the affinity of the catalyst for the substrate, which played an important role. A disubstituted tetrahydropyran synthesis could be effectively performed via kinetic resolution using ζ-hydroxyenone containing a secondary alcohol moiety using a chiral phosphoric acid catalyst.
Catalytic Asymmetric Synthesis of Quaternary Barbituric Acids
Del Pozo, Sandra,Vera, Silvia,Oiarbide, Mikel,Palomo, Claudio
, 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.