Lewis acid-catalyzed tandem acylation–Nazarov cyclization for the syntheses of fused cyclopentenones

Abstract

Treatment of N-tosylpyrroles or N-tosylindoles with α-unsubstituted α,β-unsaturated carboxylic acids or unsaturated carboxylic acids having an α electron-withdrawing substituent in the presence of TFAA and a Lewis acid catalyst resulted in the formation of fused cyclopentenones via a tandem acylation–Nazarov cyclization sequence, while either the acylation product obtained or no reaction occurred in the absence of the Lewis acid catalyst.