Enantioselective alfa-Arylation of Ketones: Application to the Synthesis of (–)-Epibatidine
2006 (English)In: Organikerdagarna, Kalmar, Sweden, 2006, Le21, P47- p.Conference paper, Presentation (Other (popular science, discussion, etc.))
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.
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-20425OAI: oai:DiVA.org:su-20425DiVA: diva2:186951
Organikerdagarna, Kalmar, Sweden
FunderSwedish Research Council