Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings

[Image: see text] A flexible approach to construct sterically congested bicyclo-alkenedione frameworks is reported. Under the action of potassium carbonate, α-sulphonyl cycloalkanones are added to functionalized allenyl esters, leading to a lactone intermediate that is subsequently reduced to initia...

Descripción completa

Detalles Bibliográficos
Autores principales: Bhat, Bilal A., Maki, Samantha L., St.Germain, Elijah J., Maity, Pradip, Lepore, Salvatore D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184455/
https://www.ncbi.nlm.nih.gov/pubmed/25184784
http://dx.doi.org/10.1021/jo501700c
_version_ 1782337842788171776
author Bhat, Bilal A.
Maki, Samantha L.
St.Germain, Elijah J.
Maity, Pradip
Lepore, Salvatore D.
author_facet Bhat, Bilal A.
Maki, Samantha L.
St.Germain, Elijah J.
Maity, Pradip
Lepore, Salvatore D.
author_sort Bhat, Bilal A.
collection PubMed
description [Image: see text] A flexible approach to construct sterically congested bicyclo-alkenedione frameworks is reported. Under the action of potassium carbonate, α-sulphonyl cycloalkanones are added to functionalized allenyl esters, leading to a lactone intermediate that is subsequently reduced to initiate an intramolecular aldol cyclization to [3.2.1], [3.3.1], and [4.3.1] bicycles. Oxidation then affords bicyclic diones in good three-step yields. Under exceptionally mild conditions, these bicycles are converted to highly functionalized medium-sized rings through a Grob-type fragmentation.
format Online
Article
Text
id pubmed-4184455
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-41844552015-09-03 Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings Bhat, Bilal A. Maki, Samantha L. St.Germain, Elijah J. Maity, Pradip Lepore, Salvatore D. J Org Chem [Image: see text] A flexible approach to construct sterically congested bicyclo-alkenedione frameworks is reported. Under the action of potassium carbonate, α-sulphonyl cycloalkanones are added to functionalized allenyl esters, leading to a lactone intermediate that is subsequently reduced to initiate an intramolecular aldol cyclization to [3.2.1], [3.3.1], and [4.3.1] bicycles. Oxidation then affords bicyclic diones in good three-step yields. Under exceptionally mild conditions, these bicycles are converted to highly functionalized medium-sized rings through a Grob-type fragmentation. American Chemical Society 2014-09-03 2014-10-03 /pmc/articles/PMC4184455/ /pubmed/25184784 http://dx.doi.org/10.1021/jo501700c Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Bhat, Bilal A.
Maki, Samantha L.
St.Germain, Elijah J.
Maity, Pradip
Lepore, Salvatore D.
Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings
title Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings
title_full Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings
title_fullStr Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings
title_full_unstemmed Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings
title_short Annulation Reactions of Allenyl Esters: An Approach to Bicyclic Diones and Medium-Sized Rings
title_sort annulation reactions of allenyl esters: an approach to bicyclic diones and medium-sized rings
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184455/
https://www.ncbi.nlm.nih.gov/pubmed/25184784
http://dx.doi.org/10.1021/jo501700c
work_keys_str_mv AT bhatbilala annulationreactionsofallenylestersanapproachtobicyclicdionesandmediumsizedrings
AT makisamanthal annulationreactionsofallenylestersanapproachtobicyclicdionesandmediumsizedrings
AT stgermainelijahj annulationreactionsofallenylestersanapproachtobicyclicdionesandmediumsizedrings
AT maitypradip annulationreactionsofallenylestersanapproachtobicyclicdionesandmediumsizedrings
AT leporesalvatored annulationreactionsofallenylestersanapproachtobicyclicdionesandmediumsizedrings

Ejemplares similares