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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, Oral presentation only (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
Identifiers
URN: urn:nbn:se:su:diva-20425OAI: oai:DiVA.org:su-20425DiVA: diva2:186951
Conference
Organikerdagarna, Kalmar, Sweden
Funder
Swedish Research Council
Available from: 2007-03-28 Created: 2007-03-28 Last updated: 2014-10-29Bibliographically approved

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CiteExportLink to record
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