Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids

Wei Yang, Xianyu Sun, Wenbo Yu, Rachita Rai, Jeffrey R. Deschamps, Lauren A. Mitchell, Chao Jiang, Alexander D. Mackerell, Fengtian Xue

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A facile synthesis of spirocyclic lactams starting from β-keto carboxylic acids via a one-pot cascade reaction involving a Curtius rearrangement and an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate is reported. The same conditions have also been used for the generation of fused cyclic lactams with similar good yields. The synthetic value of this method has been demonstrated by efficient synthesis of tetracyclic spirolactam 8 and pentacyclic spirolactam 9.

Original languageEnglish (US)
Pages (from-to)3070-3073
Number of pages4
JournalOrganic Letters
Volume17
Issue number12
DOIs
StatePublished - Jun 19 2015

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