Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Base-Catalyzed Stereospecific Isomerization of Electron-Deficient Allylic Alcohols and Ethers through Ion-Pairing
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Show others and affiliations
2016 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 138, no 40, 13408-13414 p.Article in journal (Refereed) Published
Abstract [en]

A mild base-catalyzed strategy for the isomerization of allylic alcohols and allylic ethers has been developed. Experimental and computational investigations indicate that transition metal catalysts are not required when basic additives are present. As in the case of using transition metals under basic conditions, the isomerization catalyzed solely by base also follows a stereospecific pathway. The reaction is initiated by a rate-limiting deprotonation. Formation of an intimate ion pair between an allylic anion and the conjugate acid of the base results in efficient transfer of chirality. Through this mechanism, stereochemical information contained in the allylic alcohols is transferred to the ketone products. The stereospecific isomerization is also applicable for the first time to allylic ethers, yielding synthetically valuable enantioenriched (up to 97% ee) enol ethers.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2016. Vol. 138, no 40, 13408-13414 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-136066DOI: 10.1021/jacs.6b08350ISI: 000385469600048OAI: oai:DiVA.org:su-136066DiVA: diva2:1057281
Funder
Swedish Research CouncilKnut and Alice Wallenberg FoundationVINNOVA
Available from: 2016-12-16 Created: 2016-11-29 Last updated: 2017-08-23Bibliographically approved

Open Access in DiVA

fulltext(1236 kB)6 downloads
File information
File name FULLTEXT01.pdfFile size 1236 kBChecksum SHA-512
9d7b533e26ffa4e31f527c36b9190c451924ac2301ad52e9ff0a2b822e9970a99f4b12ab8217be6d2f3ff341090c40f7a035c0752920ed6462c15720aef0b9d9
Type fulltextMimetype application/pdf

Other links

Publisher's full text

Search in DiVA

By author/editor
Martinez-Erro, SamuelSanz-Marco, AmparoGómez, Antonio BermejoVazquez-Romero, AnaMartin-Matute, Belén
By organisation
Department of Organic Chemistry
In the same journal
Journal of the American Chemical Society
Chemical Sciences

Search outside of DiVA

GoogleGoogle Scholar
Total: 6 downloads
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

Altmetric score

Total: 62 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf