SYNTHESIS Best Paper Award 2017: Asymmetric Synthesis of 2,3,4-Trisubstituted Piperidines

Tõnis Kanger highlights his award-winning paper on the asymmetric synthesis of 2,3,4-trisubstituted piperidines in an interview with SYNFORM.

The award-winning article deals with the synthesis of substituted piperidines. Piperidine is a very important scaffold in medicinal chemistry being the third most prevalent ring system in small molecule drugs. There is a huge range of variety in the biological properties of its derivatives: from the very poisonous coniine isolated from poison hemlock, that was used for the execution of ancient philosopher Socrates, to highly active compounds used in modern medicine. Therefore, it is not surprising that the synthesis of substituted piperidines has been studied thoroughly. It is known that properties of the piperidine derivatives depend on the substitution pattern of the ring. Although the synthesis of fully or densely substituted piperidines is well described, there are few examples of the synthesis of 2,3,4-trisubstituted piperidines. Another important point is stereoselectivity of the substitution. Not only relative stereochemistry but also absolute configuration of the stereocenters is of importance for biological activity. Tõnis Kanger and his co-workers disclosed a stereoselective method affording 2,3,4-trisubstituted piperidines in high diastereomeric and enantiomeric purities.


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