Change search
ReferencesLink to record
Permanent link

Direct link
Enantioselective alfa-Arylation of Ketones: Application to the Synthesis of (–)-Epibatidine
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Olofsson)
Bristol University, UK.
2006 (English)In: Organikerdagarna, Kalmar, Sweden, 2006, Le21, P47- p.Conference paper, Presentation (Other (popular science, discussion, etc.))
Abstract [en]

The enantioselective introduction of electrophiles alfa to carbonyl compounds occupies a central position in asymmetric synthesis. Although asymmetric alkylations have been well developed, high enantioselectivity in α-arylation of ketones has only been achieved in a limited number of cases.

We have developed a direct arylation reaction of cyclohexanones, employing diaryl iodonium(III) salts as electrophiles. The reaction was made enantioselective by the use of a chiral base, resulting in 2,4-substituted cyclohexanones in high yields and with high enantiomeric excesses and diastereoselectivities.

This methodology was applied in a short, enantioselective synthesis of (–)-Epibatidine, an alkaloid recently isolated from the Ecuadorian poison frog Epipedobates tricolor. The synthesis was accomplished in 6 steps and 31% overall yield, thus providing the shortest and most efficient asymmetric route to this important compound to date.

Place, publisher, year, edition, pages
2006. Le21, P47- p.
National Category
Organic Chemistry
Research subject
Organic Chemistry
URN: urn:nbn:se:su:diva-20425OAI: diva2:186951
Organikerdagarna, Kalmar, Sweden
Swedish Research Council
Available from: 2007-03-28 Created: 2007-03-28 Last updated: 2014-10-29Bibliographically approved

Open Access in DiVA

fulltext(163 kB)15 downloads
File information
File name FULLTEXT01.pdfFile size 163 kBChecksum SHA-512
Type fulltextMimetype application/pdf

Search in DiVA

By author/editor
Olofsson, Berit
By organisation
Department of Organic Chemistry
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar
Total: 15 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

Total: 30 hits
ReferencesLink to record
Permanent link

Direct link