Metalated Epoxides as Carbenoids− Further Advances in the Stereospecific Synthesis of Spirocyclopropanes

…, C Agami, E Doris, C Mioskowski

Index: Dechoux, Luc; Agami, Claude; Doris, Eric; Mioskowski, Charles European Journal of Organic Chemistry, 2001 , # 21 p. 4107 - 4110

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Citation Number: 11

Abstract

Abstract The intramolecular cyclopropanation of β, γ-unsaturated metalated epoxides derived from 11 yielded the highly strained tricyclic intermediates 7. The facile hydrolysis of the latter species afforded the α-keto spirocyclopropanes 8 in a stereospecific fashion. Indeed, the stereochemistry of the starting alkenes 11d− e governs the relative configuration of the cyclopropanes 8d− e. Furthermore, these spiro systems readily underwent acid- ...