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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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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. |
format | Online Article Text |
id | pubmed-10496134 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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