AI Article Synopsis
- Picolines and quinaldines are important compounds used in creating natural products and pharmaceuticals.
- The functionalization process for their methyl groups is typically difficult to achieve under mild conditions.
- A new method utilizing latent pronucleophiles allows for the efficient allylation of these compounds with the help of chiral Lewis base catalysts, resulting in valuable enantioenriched products that can be further converted to quinolizine-4-ones.
Article 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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| http://dx.doi.org/10.1039/d4ob01063a | DOI Listing |
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