A new approach has been developed for the synthesis of N-alkylpyrroles with a chiral substituent at the nitrogen atom by the
Paal-Knorr reaction using esters of amino acids as the source of chirality.
Keywords1,4-dicarbonyl compounds–2,5-dimethyl- and 5-aryl-2-methylpyrroles with a chiral substituent at the nitrogen atom–chiral pyrrole derivatives–iodine-catalyzed cyclization–Paal-Knorr method–Stetter reaction
[Show abstract][Hide abstract] ABSTRACT: Non-natural l-alanine derived trans-octahydrocyclohepta[b]pyrroles were synthesized with high enantiomeric purity using the aza-Cope–Mannich reaction. The study showed that the conditions of the aza-Cope–Mannich reaction and metal catalysed cyclization are mild enough to be applied to the synthesis of molecules with stereocenters, which are prone to racemization. We believe that these compounds will be of interest to medicinal chemists.
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