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N-Heterocyclic Carbene-Catalyzed Enantioselective Synthesis of Spiro-glutarimides via α,β-Unsaturated Acylazoliums. 2018

Santigopal Mondal, and Arghya Ghosh, and Subrata Mukherjee, and Akkattu T Biju
Organic Chemistry Division , CSIR-National Chemical Laboratory , Dr. Homi Bhabha Road , Pune 411008 , India.

NHC-catalyzed enantioselective [3 + 3] spiro-annulation of α,β-unsaturated aldehydes with cyclic β-ketoamides allowing the preparation of synthetically and biologically important spiro-glutarimide derivatives has been reported. The interception of the ketoamides with catalytically generated chiral α,β-unsaturated acylazoliums proceeds in a Michael addition-intramolecular amidation pathway to deliver the spirocyclic products with good yield, diastereoselectivity, and enantioselectivity.

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