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Modular, One-Pot, Sequential Aziridine Ring Opening–S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams
[Image: see text] The generation of common and stereochemically rich medium-sized benzo-fused sultams via complementary pairing of heretofore-unknown (o-fluoroaryl)sulfonyl aziridine building blocks with an array of amino alcohols/amines in a modular one-pot, sequential protocol using an aziridine r...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2015
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4943336/ https://www.ncbi.nlm.nih.gov/pubmed/26446396 http://dx.doi.org/10.1021/acs.joc.5b01429 |
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author | Loh, Joanna K. Asad, Naeem Samarakoon, Thiwanka B. Hanson, Paul R. |
author_facet | Loh, Joanna K. Asad, Naeem Samarakoon, Thiwanka B. Hanson, Paul R. |
author_sort | Loh, Joanna K. |
collection | PubMed |
description | [Image: see text] The generation of common and stereochemically rich medium-sized benzo-fused sultams via complementary pairing of heretofore-unknown (o-fluoroaryl)sulfonyl aziridine building blocks with an array of amino alcohols/amines in a modular one-pot, sequential protocol using an aziridine ring opening and intramolecular nucleophilic aromatic substitution is reported. The strategy employs a variety of amino alcohols/amines and proceeds with 6 + 4/6 + 5 and 6 + 1 cycloetherification pathways in a highly chemo- and regioselective fashion to obtain skeletally and structurally diverse, polycyclic, 10- to 11- and 7-membered benzo-fused sultams for broad-scale screening. |
format | Online Article Text |
id | pubmed-4943336 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-49433362016-10-08 Modular, One-Pot, Sequential Aziridine Ring Opening–S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams Loh, Joanna K. Asad, Naeem Samarakoon, Thiwanka B. Hanson, Paul R. J Org Chem [Image: see text] The generation of common and stereochemically rich medium-sized benzo-fused sultams via complementary pairing of heretofore-unknown (o-fluoroaryl)sulfonyl aziridine building blocks with an array of amino alcohols/amines in a modular one-pot, sequential protocol using an aziridine ring opening and intramolecular nucleophilic aromatic substitution is reported. The strategy employs a variety of amino alcohols/amines and proceeds with 6 + 4/6 + 5 and 6 + 1 cycloetherification pathways in a highly chemo- and regioselective fashion to obtain skeletally and structurally diverse, polycyclic, 10- to 11- and 7-membered benzo-fused sultams for broad-scale screening. American Chemical Society 2015-10-08 2015-10-16 /pmc/articles/PMC4943336/ /pubmed/26446396 http://dx.doi.org/10.1021/acs.joc.5b01429 Text en Copyright © 2015 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 | Loh, Joanna K. Asad, Naeem Samarakoon, Thiwanka B. Hanson, Paul R. Modular, One-Pot, Sequential Aziridine Ring Opening–S(N)Ar Strategy to 7-, 10-, and 11-Membered Benzo-Fused Sultams |
title | Modular, One-Pot, Sequential
Aziridine Ring Opening–S(N)Ar Strategy to 7-,
10-, and 11-Membered Benzo-Fused
Sultams |
title_full | Modular, One-Pot, Sequential
Aziridine Ring Opening–S(N)Ar Strategy to 7-,
10-, and 11-Membered Benzo-Fused
Sultams |
title_fullStr | Modular, One-Pot, Sequential
Aziridine Ring Opening–S(N)Ar Strategy to 7-,
10-, and 11-Membered Benzo-Fused
Sultams |
title_full_unstemmed | Modular, One-Pot, Sequential
Aziridine Ring Opening–S(N)Ar Strategy to 7-,
10-, and 11-Membered Benzo-Fused
Sultams |
title_short | Modular, One-Pot, Sequential
Aziridine Ring Opening–S(N)Ar Strategy to 7-,
10-, and 11-Membered Benzo-Fused
Sultams |
title_sort | modular, one-pot, sequential
aziridine ring opening–s(n)ar strategy to 7-,
10-, and 11-membered benzo-fused
sultams |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4943336/ https://www.ncbi.nlm.nih.gov/pubmed/26446396 http://dx.doi.org/10.1021/acs.joc.5b01429 |
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