Formation of carbon-carbon bonds via quinone methide-initiated cyclization reactions

SR Angle, DO Arnaiz, JP Boyce, RP Frutos…

Index: Angle, Steven R.; Arnaiz, Damian O.; Boyce, James P.; Frutos, Rogelio P.; Louie, Michael S.; et al. Journal of Organic Chemistry, 1994 , vol. 59, # 21 p. 6322 - 6337

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Citation Number: 34

Abstract

p-Quinone methides were found to be excellent electrophilic cyclization initiators for the formation of six-membered rings. Cyclizations to form five-and seven-membered rings were also studied. Oxidation of 2, Bdisubstituted phenols with AgzO afforded the corresponding quinone methides. A wide range of cyclization terminatorshucleophiles were found to be effective in the cyclizations, including: allylsilane, P-keto esters, furan, pyrrole, indole, and ...