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Accessing skeletal diversity under iron catalysis using substrate control: Formation of pyrroles versus lactones

AuthorsAlcaide, Benito ; Almendros, Pedro ; Quirós, M.T.
Issue Date2011
PublisherJohn Wiley & Sons
CitationAdvanced Synthesis and Catalysis 353: 585-594 (2011)
Abstract2-Azetidinone-tethered alkynols and allen-Gols, readily prepared from a propanylidene β-lactam aldehyde, were used as starting materials for divergent ring expansion reactions catalyzed by iron(III) chloride. Worthy of note, in contrast to the iron-catalyzed reactions of β-lactam allenols which lead to γ-lactones, the reaction of β-lactam alkynols under identical conditions gives pyrroles. The gold-catalyzed 6-endo aminocyclization of these allenic γ-lactones formed fused dihydropyridines. The iron-catalyzed formation of pyrroles may proceed through a Meyer-Schuster rearrangement followed by β-lactam ring opening and cyclization by attack of the amino group to the ketone. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.
Identifiersdoi: 10.1002/adsc.201100049
Appears in Collections:(IQOG) Artículos
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