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

[Image: see text] 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 diaz...

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Autores principales: Nishiura, Yuji, Gonzalez, Kevin J., Cusumano, Alexander Q., Stoltz, Brian M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10496134/
https://www.ncbi.nlm.nih.gov/pubmed/37643480
http://dx.doi.org/10.1021/acs.orglett.3c01978
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author Nishiura, Yuji
Gonzalez, Kevin J.
Cusumano, Alexander Q.
Stoltz, Brian M.
author_facet Nishiura, Yuji
Gonzalez, Kevin J.
Cusumano, Alexander Q.
Stoltz, Brian M.
author_sort Nishiura, Yuji
collection PubMed
description [Image: see text] 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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spelling pubmed-104961342023-09-13 Enantioselective 1,3-Dipolar Cycloadditions of α-Methylene Lactams to Construct Spirocycles Nishiura, Yuji Gonzalez, Kevin J. Cusumano, Alexander Q. Stoltz, Brian M. Org Lett [Image: see text] 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. American Chemical Society 2023-08-29 /pmc/articles/PMC10496134/ /pubmed/37643480 http://dx.doi.org/10.1021/acs.orglett.3c01978 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Nishiura, Yuji
Gonzalez, Kevin J.
Cusumano, Alexander Q.
Stoltz, Brian M.
Enantioselective 1,3-Dipolar Cycloadditions of α-Methylene Lactams to Construct Spirocycles
title Enantioselective 1,3-Dipolar Cycloadditions of α-Methylene Lactams to Construct Spirocycles
title_full Enantioselective 1,3-Dipolar Cycloadditions of α-Methylene Lactams to Construct Spirocycles
title_fullStr Enantioselective 1,3-Dipolar Cycloadditions of α-Methylene Lactams to Construct Spirocycles
title_full_unstemmed Enantioselective 1,3-Dipolar Cycloadditions of α-Methylene Lactams to Construct Spirocycles
title_short Enantioselective 1,3-Dipolar Cycloadditions of α-Methylene Lactams to Construct Spirocycles
title_sort enantioselective 1,3-dipolar cycloadditions of α-methylene lactams to construct spirocycles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10496134/
https://www.ncbi.nlm.nih.gov/pubmed/37643480
http://dx.doi.org/10.1021/acs.orglett.3c01978
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