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The First Examples of Nazarov Cyclizations Leading to Annulated Pyrroles

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journal contribution
posted on 05.01.2006, 00:00 by Chuanjun Song, David W. Knight, Maria A. Whatton
Reactions between α-substituted unsaturated carboxylic acids 20 and N-tosylpyrroles [14, 23] in the presence of trifluoroacetic anhydride result in smooth α-acylation of the pyrrole, followed by Nazarov cyclization to give 50−80% yields of cyclopenta[b]pyrroles. The presence of an α-substituent in the unsaturated acid appears to be mandatory.