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A General Catalytic Route to Enantioenriched Isoindolinones and Phthalides: Application in the Synthesis of ( S)-PD 172938.

Chiral Brønsted acid catalyzed enantioselective syntheses of isoindolinones and phthalides have been accomplished via tandem Mannich-lactamization and aldol-lactonization reactions, respectively. A variety of enantioenriched isoindolinones (up to 99% ee) and phthalides (up to 85% ee) containing α-diazoesters were afforded in excellent yields. Furthermore, a concise synthesis of ( S)-PD 172938 has been demonstrated by using this protocol.