Enantioselective 1,3-Dipolar Cycloadditions of α‑Methylene Lactams to Construct Spirocycles

Spirocyclic scaffolds are important motifs due to their potential to bestow favorable effects on pharmaceutical compounds. However, there is a need for efficient methods for their enantioselective construction. We report a method for the asymmetric 1,3-dipolar cycloaddition of diazoacetates or nitri...

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Bibliographic Details
Published inOrganic letters Vol. 25; no. 35; pp. 6469 - 6473
Main Authors Nishiura, Yuji, Gonzalez, Kevin J., Cusumano, Alexander Q., Stoltz, Brian M.
Format Journal Article
LanguageEnglish
Published American Chemical Society 08.09.2023
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Letter
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Summary:Spirocyclic scaffolds are important motifs due to their potential to bestow favorable effects on pharmaceutical compounds. However, there is a need for efficient methods for their enantioselective construction. We report a method for the asymmetric 1,3-dipolar cycloaddition of diazoacetates or nitrile oxides with α-methylene lactams to prepare chiral spirocyclic heterocycles. The methodology is high yielding (up to 91% yield) and enantioselective (up to 89% ee) for a wide range of N-substituents and 6- and 7-membered ring lactam substrates.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c01978