Multicomponent Diastereoselective Synthesis of Indolizidines via 1,3-Dipolar Cycloadditions of Azomethine Ylides

Dedicated to Professor Dieter Enders.

Abstract

The synthesis of polyfunctionalized indolizidines from pipecolinic acid alkyl ester derivatives, aldehydes and a wide range of dipolarophiles by multicomponent 1,3-dipolar cycloadditions is developed in a diastereoselective manner. The cycloadditions take place in toluene with short reaction times at 70 °C, giving good yields. The synthesis of these fused heterocycles is also studied starting from pipecolinic acid, generating the dipole through a decarboxylative route at 120 °C. The relative configuration of the resulting products as well as the mechanistic pathways are also explained.

Key words

cycloaddition - multicomponent - indolizidines - azomethine ylides - iminium route - decarboxylative route

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