lnu.sePublications
Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • 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
Practical one-pot stereospecific preparation of vicinal and 1,3-diols
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Univ Western Australia, Australia.
Univ Western Australia, Australia.
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences.ORCID iD: 0000-0001-7158-6393
2017 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 58, no 1, 75-77 p.Article in journal (Refereed) Published
Abstract [en]

A facile one-pot synthesis providing vicinal diols and 1,3-diols in >95% stereoisomeric purity from commercially available enantiopure hydroxy esters has been developed. The esters were reduced with DIBALH and alkylated in situ with 4-pentenylmagnesium bromide, which after workup generated the title diols as diastereomeric pairs. These pairs were easily separated by preparative chromatography, affording products with retained stereoisomeric purity from the starting materials. This method represents an expedient preparation of many common natural products, such as cerambycid beetle pheromones and intermediates towards bicyclic acetal bark beetle pheromones. (C) 2016 Elsevier Ltd. All rights reserved.

Place, publisher, year, edition, pages
2017. Vol. 58, no 1, 75-77 p.
Keyword [en]
Diols, DIBALH, Grignard, Acetals, Pheromone
National Category
Biological Sciences
Research subject
Natural Science, Ecological chemistry
Identifiers
URN: urn:nbn:se:lnu:diva-60803DOI: 10.1016/j.tetlet.2016.11.101ISI: 000392038800018OAI: oai:DiVA.org:lnu-60803DiVA: diva2:1075958
Available from: 2017-02-21 Created: 2017-02-21 Last updated: 2017-02-21Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text

Search in DiVA

By author/editor
Bohman, BjörnUnelius, C. Rikard
By organisation
Department of Chemistry and Biomedical Sciences
In the same journal
Tetrahedron Letters
Biological Sciences

Search outside of DiVA

GoogleGoogle Scholar

Altmetric score

Total: 1 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • 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