ALKENYL IMINIUM ION IN DIELS-ALDER REACTION: SYNTHESIS OF HIGHLY SUBSTITUTED N-HETEROCYCLES

TL;DRAbstract

Heterocyclic structures are critical components of an extensive collection of chemotherapeutic agents, either in service or under development, for treating numerous human illnesses. As a result, reaction technologies for heterocycle construction, in the context of both target- and diversity-oriented synthesis, enjoy a particularly prominent role in medicinal chemistry. Amongst all the C-C bond forming reactions, the classic Diels-Alder cycloaddition remains one of the most powerful transformations in organic chemistry especially for the formation of heterocyclic structures. Herein, we report a new methodology based on inverse electron demand Diels-Alder reaction utilizing reactive "N-alkenyl iminium ion" and a suitable dienophile for the stereoselective synthesis of substituted piperidine derivatives. In presence of a suitable Lewis acid, the "N-alkenyl iminium ion" is generated from the respective enamine-aminal derivative in situ and undergoes Diels-Alder reaction with a dienophile p

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