As an initial target, the phthalidyl ester product 41 derived from Indomethacin was targeted, as this would generate an enantioenriched tetra-substituted C(3)-t-Bu analogue of the known prodrug Talmetacin. Treatment of (±)-30 under these standard reaction conditions gave the desired product ester 41 in 70% yield and 97:3 er. The generality of this approach was then examplified, with the tetra-substituted phthalidyl ester products 42-47 derived from Isoxepac, Probenecid, Oxaprozin, linoleic acid, Febuxostat and Fenbuprofen respectively all generated in excellent yields and in ≥94:6 er, clearly demonstrating the functional group tolerance of this methodology.