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A General Catalytic Route to Enantioenriched Isoindolinones and Phthalides: Application in the Synthesis of (S)-PD 172938
- Ray, Sumit K., Sadhu, Milon M., Biswas, Rayhan G., Unhale, Rajshekhar A., Singh, Vinod K.
- Organic letters 2019 v.21 no.2 pp. 417-422
- Bronsted acids, chemical reactions, chemical structure, phthalides
- 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.