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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Enantioselective Lewis base catalysed allylation of picoline- and quinaldine-based latent pronucleophiles
Markus Lange1, Nikita Alistratov1, Ivan Vilotijevic1
1Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstrasse 10, 07743 Jena, Germany. ivan.vilotijevic@uni-jena.de.
Abstract:
Picolines and quinaldines are valuable building blocks and intermediates in the synthesis of natural products and pharmaceuticals. Functionalization of the methyl group in picolines and quinaldines under mild conditions is challenging. We report that the concept of latent pronucleophiles enables Lewis base catalysed allylation of picolines and quinaldines with allylic fluorides starting from silylated picolines and quinaldines. Reactions afford enantioenriched allylation products when chiral Lewis base catalysts are used. The allylation products can be rapidly transformed to quinolizine-4-ones.
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