[reaction: see text] Reactions between alpha-substituted unsaturated carboxylic acids 20 and N-tosylpyrroles [14, 23] in the presence of trifluoroacetic anhydride result in smooth alpha-acylation of the pyrrole, followed by Nazarov cyclization to give 50-80% yields of cyclopenta[b]pyrroles. The presence of an alpha-substituent in the unsaturated acid appears to be mandatory.
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and trifluoroacetic anhydride proceeds highly regioselectively. The 2-acylated derivatives are produced with little or none of the isomeric 3-acyl isomers. -(SONG, C.; KNIGHT*, D. W.; WHATTON, M. A.; Tetrahedron Lett. 45 (2004) 52, 9573-9576; Sch. Chem., Cardiff Univ., Cardiff CF1 3TB, UK; Eng.) -Mais 15-104
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