The chiral oxazolones are structural subunits in numerous natural products and designed molecules with substantial pharmacological interests. Even though asymmetric C-C forming reactions of simple oxazolones with an electrophilic reactant might in principle constitute a viable way to this type of chiral synthons, to date there has been no examples documented in the literature. In this work, a palladium-catalyzed regio- enantioselective allylic alkylation of 4-substituted-2(3H)-ones with Morita–Baylis–Hillman adducts has been developed using a spiroketal-based diphosphine (SKP) as the ligand, thus affording a range of chiral 4,5-substituted-2(3H)-ones products in high yields (72%-99%) with good to excellent chemo-, regio-, and enantioselectivities (B/L 91:9-&gt;99:1, C-/N- 95:5-&gt;99:1, 85-98% ee). The synthesis can be readily scaled up to gram scale under fairly low catalyst loadings, and the utility of the protocol was showcased in the facile transformation of the products into more elaborated chiral molecules.

Palladium-catalyzed regioselective asymmetric C-allylation of oxazolones with Morita–Baylis–Hillman adducts

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