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An efficient and diastereoselective (CDC)-Rh-catalyzed hydroalkylation of dienes with 1,3-oxazol-5(4 H )-ones is reported. Aryl and alkyl substituted dienes are converted to α,α-substituted oxazolones (24 examples) by the formation of N -substituted quaternary carbon stereogenic centers in good yields (up to 96%) and with high diastereoselectivity (&gt;20 : 1 dr). The reaction is tolerant of a range of dienes and oxazolones bearing various functional groups. Utility of the oxazolone products is illustrated through hydrolysis to form α,β-substituted α-amino acid analogues and stereoselective epoxidation of the resultant alkene to create four contiguous stereocenters.

Diastereoselective synthesis of vicinal tertiary and N-substituted quaternary stereogenic centers by catalytic hydroalkylation of dienes