Oxa-Michael-initiated cascade reactions of levoglucosenone

The reactions of aromatic aldehydes and levoglucosenone promoted by methoxide gives bridged α,β-unsaturated ketones, formed by a series of oxa-Michael-initiated cascade reactions in yields of up to 91% (14 examples). A complex series of equilibria operate during the reaction, and the formation of th...

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Autores principales: Klepp, Julian, Bousfield, Thomas, Cummins, Hugh, Legendre, Sarah V A-M, Camp, Jason E, Greatrex, Ben W
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/PMC9577383/
https://www.ncbi.nlm.nih.gov/pubmed/36300013
http://dx.doi.org/10.3762/bjoc.18.151
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author Klepp, Julian
Bousfield, Thomas
Cummins, Hugh
Legendre, Sarah V A-M
Camp, Jason E
Greatrex, Ben W
author_facet Klepp, Julian
Bousfield, Thomas
Cummins, Hugh
Legendre, Sarah V A-M
Camp, Jason E
Greatrex, Ben W
author_sort Klepp, Julian
collection PubMed
description The reactions of aromatic aldehydes and levoglucosenone promoted by methoxide gives bridged α,β-unsaturated ketones, formed by a series of oxa-Michael-initiated cascade reactions in yields of up to 91% (14 examples). A complex series of equilibria operate during the reaction, and the formation of the bridged species is thermodynamically favored, except in the case of 5-methylfurfural and pyrrole-2-carboxaldehyde. This is the first report detailing this type of aldol/Michael cascade involving oxa-Michael initiation.
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spelling pubmed-95773832022-10-25 Oxa-Michael-initiated cascade reactions of levoglucosenone Klepp, Julian Bousfield, Thomas Cummins, Hugh Legendre, Sarah V A-M Camp, Jason E Greatrex, Ben W Beilstein J Org Chem Full Research Paper The reactions of aromatic aldehydes and levoglucosenone promoted by methoxide gives bridged α,β-unsaturated ketones, formed by a series of oxa-Michael-initiated cascade reactions in yields of up to 91% (14 examples). A complex series of equilibria operate during the reaction, and the formation of the bridged species is thermodynamically favored, except in the case of 5-methylfurfural and pyrrole-2-carboxaldehyde. This is the first report detailing this type of aldol/Michael cascade involving oxa-Michael initiation. Beilstein-Institut 2022-10-13 /pmc/articles/PMC9577383/ /pubmed/36300013 http://dx.doi.org/10.3762/bjoc.18.151 Text en Copyright © 2022, Klepp 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
Klepp, Julian
Bousfield, Thomas
Cummins, Hugh
Legendre, Sarah V A-M
Camp, Jason E
Greatrex, Ben W
Oxa-Michael-initiated cascade reactions of levoglucosenone
title Oxa-Michael-initiated cascade reactions of levoglucosenone
title_full Oxa-Michael-initiated cascade reactions of levoglucosenone
title_fullStr Oxa-Michael-initiated cascade reactions of levoglucosenone
title_full_unstemmed Oxa-Michael-initiated cascade reactions of levoglucosenone
title_short Oxa-Michael-initiated cascade reactions of levoglucosenone
title_sort oxa-michael-initiated cascade reactions of levoglucosenone
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9577383/
https://www.ncbi.nlm.nih.gov/pubmed/36300013
http://dx.doi.org/10.3762/bjoc.18.151
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