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Synthesis of 1-Azaspiro[4.4]nonane Derivatives Enabled by Domino Radical Bicyclization Involving Formation and Capture of Alkoxyaminyl Radicals
[Image: see text] The application of a domino radical bicyclization for the synthesis of compounds containing the 1-azaspiro[4.4]nonane skeleton in 11–67% yields as a mixture of diastereomers is described (trans configuration preference). This process involved formation and capture of alkoxyaminyl r...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6921261/ https://www.ncbi.nlm.nih.gov/pubmed/31867503 http://dx.doi.org/10.1021/acsomega.9b02515 |
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author | Guerrero-Caicedo, Alejandro Soto-Martínez, Diana M. Osorio, David A. Novoa, Muskendol Loaiza, Alix E. Jaramillo-Gómez, Luz M. |
author_facet | Guerrero-Caicedo, Alejandro Soto-Martínez, Diana M. Osorio, David A. Novoa, Muskendol Loaiza, Alix E. Jaramillo-Gómez, Luz M. |
author_sort | Guerrero-Caicedo, Alejandro |
collection | PubMed |
description | [Image: see text] The application of a domino radical bicyclization for the synthesis of compounds containing the 1-azaspiro[4.4]nonane skeleton in 11–67% yields as a mixture of diastereomers is described (trans configuration preference). This process involved formation and capture of alkoxyaminyl radicals. For this purpose, O-benzyl oxime ethers with a brominated or iodinated aromatic ring or a terminal alkynyl group and an alkenyl moiety were employed as starting materials. The bicyclization was initiated by 2,2′-azobisisobutyronitrile or triethylborane and promoted by Bu(3)SnH. The best results were obtained with O-benzyl oxime ethers containing an alkenyl moiety tethered to electron withdrawing groups or aryl substituents, whereas oxime radical precursor attached to methyl-substituted olefin precluded the capture of alkoxyaminyl radical, giving rise mainly to monocyclized product. |
format | Online Article Text |
id | pubmed-6921261 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-69212612019-12-20 Synthesis of 1-Azaspiro[4.4]nonane Derivatives Enabled by Domino Radical Bicyclization Involving Formation and Capture of Alkoxyaminyl Radicals Guerrero-Caicedo, Alejandro Soto-Martínez, Diana M. Osorio, David A. Novoa, Muskendol Loaiza, Alix E. Jaramillo-Gómez, Luz M. ACS Omega [Image: see text] The application of a domino radical bicyclization for the synthesis of compounds containing the 1-azaspiro[4.4]nonane skeleton in 11–67% yields as a mixture of diastereomers is described (trans configuration preference). This process involved formation and capture of alkoxyaminyl radicals. For this purpose, O-benzyl oxime ethers with a brominated or iodinated aromatic ring or a terminal alkynyl group and an alkenyl moiety were employed as starting materials. The bicyclization was initiated by 2,2′-azobisisobutyronitrile or triethylborane and promoted by Bu(3)SnH. The best results were obtained with O-benzyl oxime ethers containing an alkenyl moiety tethered to electron withdrawing groups or aryl substituents, whereas oxime radical precursor attached to methyl-substituted olefin precluded the capture of alkoxyaminyl radical, giving rise mainly to monocyclized product. American Chemical Society 2019-12-04 /pmc/articles/PMC6921261/ /pubmed/31867503 http://dx.doi.org/10.1021/acsomega.9b02515 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Guerrero-Caicedo, Alejandro Soto-Martínez, Diana M. Osorio, David A. Novoa, Muskendol Loaiza, Alix E. Jaramillo-Gómez, Luz M. Synthesis of 1-Azaspiro[4.4]nonane Derivatives Enabled by Domino Radical Bicyclization Involving Formation and Capture of Alkoxyaminyl Radicals |
title | Synthesis of 1-Azaspiro[4.4]nonane
Derivatives
Enabled by Domino Radical Bicyclization Involving Formation and Capture
of Alkoxyaminyl Radicals |
title_full | Synthesis of 1-Azaspiro[4.4]nonane
Derivatives
Enabled by Domino Radical Bicyclization Involving Formation and Capture
of Alkoxyaminyl Radicals |
title_fullStr | Synthesis of 1-Azaspiro[4.4]nonane
Derivatives
Enabled by Domino Radical Bicyclization Involving Formation and Capture
of Alkoxyaminyl Radicals |
title_full_unstemmed | Synthesis of 1-Azaspiro[4.4]nonane
Derivatives
Enabled by Domino Radical Bicyclization Involving Formation and Capture
of Alkoxyaminyl Radicals |
title_short | Synthesis of 1-Azaspiro[4.4]nonane
Derivatives
Enabled by Domino Radical Bicyclization Involving Formation and Capture
of Alkoxyaminyl Radicals |
title_sort | synthesis of 1-azaspiro[4.4]nonane
derivatives
enabled by domino radical bicyclization involving formation and capture
of alkoxyaminyl radicals |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6921261/ https://www.ncbi.nlm.nih.gov/pubmed/31867503 http://dx.doi.org/10.1021/acsomega.9b02515 |
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