Tandem Michael-carbene insertion reactions of alkynyliodonium salts. Extremely efficient cyclopentene annulations

M Ochiai, M Kunishima, Y Nagao, K Fuji…

Index: Ochiai, Masahito; Kunishima, Munetaka; Nagao, Yoshimitsu; Fuji, Kaoru; Shiro, Motoo; Fujita, Eiichi Journal of the American Chemical Society, 1986 , vol. 108, p. 8281 - 8283

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Citation Number: 110

Abstract

Intramolecular carbon-hydrogen insertion reactions of carbenes have proven to be powerful and invaluable tools in the synthesis of highly functionalized, five-membered ring systems.* We report herein a novel and potentially highly versatile cyclopentene annulation utilizing hypervalent organoiodine (II1) compounds, alkynyliodonium salts, via the tandem Michael- carbene insertion (MCI) reaction (Scheme I).