NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones

Thiazolium carbene-catalyzed reactions of 1,2-diketones and 1,2,3-triketones with enones and ynones have been investigated. The diketones gave α,β-double acylation products via unique Breslow intermediates isolable as acid salts, whereas the triketones formed stable adducts with the NHC instead of t...

Descripción completa

Detalles Bibliográficos
Autores principales: Takaki, Ken, Hino, Makoto, Ohno, Akira, Komeyama, Kimihiro, Yoshida, Hiroto, Fukuoka, Hiroshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5588593/
https://www.ncbi.nlm.nih.gov/pubmed/28904625
http://dx.doi.org/10.3762/bjoc.13.176
_version_ 1783262204346236928
author Takaki, Ken
Hino, Makoto
Ohno, Akira
Komeyama, Kimihiro
Yoshida, Hiroto
Fukuoka, Hiroshi
author_facet Takaki, Ken
Hino, Makoto
Ohno, Akira
Komeyama, Kimihiro
Yoshida, Hiroto
Fukuoka, Hiroshi
author_sort Takaki, Ken
collection PubMed
description Thiazolium carbene-catalyzed reactions of 1,2-diketones and 1,2,3-triketones with enones and ynones have been investigated. The diketones gave α,β-double acylation products via unique Breslow intermediates isolable as acid salts, whereas the triketones formed stable adducts with the NHC instead of the coupling products.
format Online
Article
Text
id pubmed-5588593
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-55885932017-09-13 NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones Takaki, Ken Hino, Makoto Ohno, Akira Komeyama, Kimihiro Yoshida, Hiroto Fukuoka, Hiroshi Beilstein J Org Chem Full Research Paper Thiazolium carbene-catalyzed reactions of 1,2-diketones and 1,2,3-triketones with enones and ynones have been investigated. The diketones gave α,β-double acylation products via unique Breslow intermediates isolable as acid salts, whereas the triketones formed stable adducts with the NHC instead of the coupling products. Beilstein-Institut 2017-08-30 /pmc/articles/PMC5588593/ /pubmed/28904625 http://dx.doi.org/10.3762/bjoc.13.176 Text en Copyright © 2017, Takaki et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Takaki, Ken
Hino, Makoto
Ohno, Akira
Komeyama, Kimihiro
Yoshida, Hiroto
Fukuoka, Hiroshi
NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones
title NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones
title_full NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones
title_fullStr NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones
title_full_unstemmed NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones
title_short NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones
title_sort nhc-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5588593/
https://www.ncbi.nlm.nih.gov/pubmed/28904625
http://dx.doi.org/10.3762/bjoc.13.176
work_keys_str_mv AT takakiken nhccatalyzedcleavageofvicinaldiketonesandtriketonesfollowedbyinsertionofenonesandynones
AT hinomakoto nhccatalyzedcleavageofvicinaldiketonesandtriketonesfollowedbyinsertionofenonesandynones
AT ohnoakira nhccatalyzedcleavageofvicinaldiketonesandtriketonesfollowedbyinsertionofenonesandynones
AT komeyamakimihiro nhccatalyzedcleavageofvicinaldiketonesandtriketonesfollowedbyinsertionofenonesandynones
AT yoshidahiroto nhccatalyzedcleavageofvicinaldiketonesandtriketonesfollowedbyinsertionofenonesandynones
AT fukuokahiroshi nhccatalyzedcleavageofvicinaldiketonesandtriketonesfollowedbyinsertionofenonesandynones

Ejemplares similares