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J Org Chem. 2019 May 3;84(9):5313-5327. doi: 10.1021/acs.joc.9b00320. Epub 2019 Mar 29.

Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (-)-Paroxetine.

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School of Chemical Sciences , Indian Association for the Cultivation of Science , 2A & 2B Raja S. C. Mullick Road , Jadavpur, Kolkata 700032 , India.


A simple yet highly effective approach toward enantioselective synthesis of trans-3,4-disubstituted glutarimides from readily available starting materials is developed using oxidative N-heterocyclic carbene catalysis. The catalytic reaction involves a formal [3 + 3] annulation between enals and substituted malonamides enabling the production of glutarimide derivatives in a single chemical operation via concomitant formation of C-C and C-N bonds. The reaction offers easy access to a broad range of functionalized glutarimides with excellent enantioselectivity and good yield. Synthetic application of the method is demonstrated via formal synthesis of (-)-paroxetine and other bioactive molecules.


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