N-Heterocyclic Carbene-Catalyzed Enantioselective Synthesis of Carbocycle-Fused Uracils via Formal [4 + 2] Annulation/Lactone Formation/Decarboxylation Cascade
Lin Chen, Simiao Zhang, Jingyi Wang, Lei Chen, Yi‐Wei Zhu, Ding Du
Abstract
An unprecedented organocatalytic asymmetric construction of novel six-membered carbocycle fused uracils has been demonstrated by the reaction of the remotely enolizable 6-methyluracil-5-carbaldehydes with 2-bromoenals. The reaction involves an N-heterocyclic carbene-catalyzed formal [4 + 2] annulation of o-quinodimethane (oQDM) dienolates with α,β-unsaturated acylazoliums, followed by a cascade lactone formation/decarboxylation process. This protocol unlocks a new platform to access enantioenriched carbocycle-fused uracils.
Topics & Concepts
DecarboxylationChemistryAnnulationCarbeneEnantioselective synthesisCatalysisStereochemistryCombinatorial chemistryOrganic chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistrySynthetic Organic Chemistry MethodsOrganoboron and organosilicon chemistry