Palladium-Catalyzed Asymmetric (3 + 2) Cycloaddition of 5-Allenyloxazolidine-2,4-Diones with Barbiturate-Derived Alkenes: Synthesis of Spirobarbiturate-γ-Lactams
Yujie Dong, Jun Liu, Kuan Li, Sheng Han, Bo Liang, Fazhou Yang, Songcheng Yu, Yongjun Wu, Cheng Zhang, Hongchao Guo
Abstract
The 5-allenyloxazolidine-2,4-diones had been synthesized as novel precursors of π-allyl palladium zwitterion and were applied in a palladium-catalyzed enantioselective (3 + 2) annulation by using barbiturate-derived alkenes as the reaction partner in the presence of an axially chiral phosphoramidite ligand. This reaction proceeded smoothly under mild reaction conditions, affording highly functionalized spirobarbiturate-γ-lactam derivatives in excellent yields along with high diastereo- and enantioselectivities. The scale-up reaction and further transformation of the product were also successful.
Topics & Concepts
ChemistryAnnulationPalladiumPhosphoramiditeCatalysisEnantioselective synthesisLigand (biochemistry)Combinatorial chemistryCycloadditionZwitterionOrganic chemistryMedicinal chemistryMoleculeReceptorDNABiochemistryOligonucleotideAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization Methods