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

B Alcaide, P Almendros, JM Alonso…

Index: Alcaide, Benito; Almendros, Pedro; Quiros, M. Teresa; Lopez, Ramon; Menendez, Maria I.; Sochacka-Cwikla, Aleksandra Journal of the American Chemical Society, 2013 , vol. 135, # 2 p. 898 - 905

Full Text: HTML

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 ...