1292293-84-5Relevant articles and documents
Accessing skeletal diversity under iron catalysis using substrate control: Formation of pyrroles versus lactones
Alcaide, Benito,Almendros, Pedro,Quiros, M. Teresa
, p. 585 - 594 (2011/04/25)
2-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.
