Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates

[Image: see text] Donor–acceptor cyclopropanes with two geminal carboxylic esters are reacted with chalcogenyl chlorides and bromides to afford ring-opened products bearing the halogen atoms in the 1-position, adjacent to the donor, and the chalcogenyl residue in the 3-position next to the two accep...

Descripción completa

Detalles Bibliográficos
Autores principales: Wallbaum, Jan, Garve, Lennart K. B., Jones, Peter G., Werz, Daniel B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5223275/
https://www.ncbi.nlm.nih.gov/pubmed/27966993
http://dx.doi.org/10.1021/acs.orglett.6b03375
_version_ 1782493137339416576
author Wallbaum, Jan
Garve, Lennart K. B.
Jones, Peter G.
Werz, Daniel B.
author_facet Wallbaum, Jan
Garve, Lennart K. B.
Jones, Peter G.
Werz, Daniel B.
author_sort Wallbaum, Jan
collection PubMed
description [Image: see text] Donor–acceptor cyclopropanes with two geminal carboxylic esters are reacted with chalcogenyl chlorides and bromides to afford ring-opened products bearing the halogen atoms in the 1-position, adjacent to the donor, and the chalcogenyl residue in the 3-position next to the two acceptor groups. A variety of different donors (e.g., aryl, N, and O) are used. The stereospecificity of the reaction is demonstrated by using a chiral starting material.
format Online
Article
Text
id pubmed-5223275
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-52232752017-01-11 Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates Wallbaum, Jan Garve, Lennart K. B. Jones, Peter G. Werz, Daniel B. Org Lett [Image: see text] Donor–acceptor cyclopropanes with two geminal carboxylic esters are reacted with chalcogenyl chlorides and bromides to afford ring-opened products bearing the halogen atoms in the 1-position, adjacent to the donor, and the chalcogenyl residue in the 3-position next to the two acceptor groups. A variety of different donors (e.g., aryl, N, and O) are used. The stereospecificity of the reaction is demonstrated by using a chiral starting material. American Chemical Society 2016-12-14 2017-01-06 /pmc/articles/PMC5223275/ /pubmed/27966993 http://dx.doi.org/10.1021/acs.orglett.6b03375 Text en Copyright © 2016 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 Wallbaum, Jan
Garve, Lennart K. B.
Jones, Peter G.
Werz, Daniel B.
Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates
title Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates
title_full Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates
title_fullStr Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates
title_full_unstemmed Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates
title_short Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates
title_sort ring-opening 1,3-halochalcogenation of cyclopropane dicarboxylates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5223275/
https://www.ncbi.nlm.nih.gov/pubmed/27966993
http://dx.doi.org/10.1021/acs.orglett.6b03375
work_keys_str_mv AT wallbaumjan ringopening13halochalcogenationofcyclopropanedicarboxylates
AT garvelennartkb ringopening13halochalcogenationofcyclopropanedicarboxylates
AT jonespeterg ringopening13halochalcogenationofcyclopropanedicarboxylates
AT werzdanielb ringopening13halochalcogenationofcyclopropanedicarboxylates

Ejemplares similares