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Ethyl 5-[(4-methylphenyl)sulfonyl]-3-oxopentanoate: A Bench-Stable Precursor for Nazarov's Reagent

By: Dr. Mark Redlich, Chemfiles Volume 10 Article 1

Nazarov's reagent is a commonly used annulating agent, but its synthesis is often fraught with poor yields or difficulties isolating the material. De Risi and coworkers recently reported the synthesis and application of ethyl 5-[(4-methylphenyl)sulfonyl]- 3-oxopentanoate, which is a bench-stable powder that can be stored at room temperature without any special precautions, and demasked under various conditions to form ethyl 3-oxopent- 4-enoate (Nazarov's reagent) in situ to generate annulated products (Scheme 6).1

Scheme 6

Scheme 6: (718327)

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  1. Benetti, S. et al. Synlett 2008, 2609.

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