A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition

A straightforward access to novel spiro[benzofuran-2,3'-pyrrolidine]-2',5'-diones based on the Rh(2)(esp)(2)-catalyzed insertion of carbenes derived from diazo arylidene succinimides (DAS) into the O–H bond of phenols is described. The initial adducts underwent a thermally promoted Cl...

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Autores principales: Vepreva, Anastasia, Yanovich, Alexander, Dar’in, Dmitry, Kantin, Grigory, Bunev, Alexander, Krasavin, Mikhail
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9749547/
https://www.ncbi.nlm.nih.gov/pubmed/36570564
http://dx.doi.org/10.3762/bjoc.18.177
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author Vepreva, Anastasia
Yanovich, Alexander
Dar’in, Dmitry
Kantin, Grigory
Bunev, Alexander
Krasavin, Mikhail
author_facet Vepreva, Anastasia
Yanovich, Alexander
Dar’in, Dmitry
Kantin, Grigory
Bunev, Alexander
Krasavin, Mikhail
author_sort Vepreva, Anastasia
collection PubMed
description A straightforward access to novel spiro[benzofuran-2,3'-pyrrolidine]-2',5'-diones based on the Rh(2)(esp)(2)-catalyzed insertion of carbenes derived from diazo arylidene succinimides (DAS) into the O–H bond of phenols is described. The initial adducts underwent a thermally promoted Claisen rearrangement followed by DABCO-catalyzed intramolecular 5-exo-trig oxa-Michael addition.
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spelling pubmed-97495472022-12-23 A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition Vepreva, Anastasia Yanovich, Alexander Dar’in, Dmitry Kantin, Grigory Bunev, Alexander Krasavin, Mikhail Beilstein J Org Chem Full Research Paper A straightforward access to novel spiro[benzofuran-2,3'-pyrrolidine]-2',5'-diones based on the Rh(2)(esp)(2)-catalyzed insertion of carbenes derived from diazo arylidene succinimides (DAS) into the O–H bond of phenols is described. The initial adducts underwent a thermally promoted Claisen rearrangement followed by DABCO-catalyzed intramolecular 5-exo-trig oxa-Michael addition. Beilstein-Institut 2022-12-06 /pmc/articles/PMC9749547/ /pubmed/36570564 http://dx.doi.org/10.3762/bjoc.18.177 Text en Copyright © 2022, Vepreva et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Vepreva, Anastasia
Yanovich, Alexander
Dar’in, Dmitry
Kantin, Grigory
Bunev, Alexander
Krasavin, Mikhail
A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition
title A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition
title_full A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition
title_fullStr A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition
title_full_unstemmed A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition
title_short A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition
title_sort novel spirocyclic scaffold accessed via tandem claisen rearrangement/intramolecular oxa-michael addition
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9749547/
https://www.ncbi.nlm.nih.gov/pubmed/36570564
http://dx.doi.org/10.3762/bjoc.18.177
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