Asymmetric α-Regioselective [3+2] Annulation of Morita-Baylis-Hillman Carbonates: Construction of Three Contiguous Stereocenters with Vicinal Quaternary Carbon Centers

Asymmetric alpha-regioselective annulation of MBH carbonates with 4-arylmethylisoxazol-S-ones has been developed to afford spirocyclic oxindole derivatives containing three contiguous stereogenic centers and vicinal all-carbon quaternary chiral centers. This reaction exhibits a broad substrate scope and excellent functional group tolerance. Excellent yields with high diastereoand enantioselectivities were obtained in this efficient organocatalytic reaction.

Automated summary

The asymmetric alpha-regioselective annulation of MBH carbonates with 4-arylmethylisoxazol-S-ones has been developed, resulting in the synthesis of spirocyclic oxindole derivatives with three contiguous stereogenic centers and vicinal all-carbon quaternary chiral centers. This reaction exhibits a broad substrate scope and excellent functional group tolerance, producing high yields with high diastereo- and enantioselectivities.