Carbocyclization versus oxycyclization on the metal-catalyzed reactions of oxyallenyl C3-linked índoles

…, P Almendros, JM Alonso, I Fernandez

Index: Alcaide, Benito; Almendros, Pedro; Alonso, Jose M.; Fernandez, Israel Journal of Organic Chemistry, 2013 , vol. 78, # 13 p. 6688 - 6701

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Citation Number: 27

Abstract

The preparation of previously unknown (indol-3-yl)-α-allenols and-allenones was accomplished from indole-3-carbaldehydes, through indium-mediated Barbier allenylation reaction taking advantage of the N-(2-pyridyl) sulfonyl group. Metal-catalyzed cyclizations of oxyallenyl C3-linked indoles proceeded in two ways depending on the presence or absence of the N-(2-pyridyl) sulfonyl group. For allenols, gold-catalyzed oxycyclization occurred in ...