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Zinc-mediated anionic cyclization of unstabilized ketone enolates with unactivated alkenes

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Abstract We report herein general conditions for a zinc-mediated anionic cyclization of unstabilized ketone enolates. This anionic cyclization allows access to various carbocyclic architectures by utilizing abundant ketones and unactivated… Click to show full abstract

Abstract We report herein general conditions for a zinc-mediated anionic cyclization of unstabilized ketone enolates. This anionic cyclization allows access to various carbocyclic architectures by utilizing abundant ketones and unactivated alkenes as precursors. The transformation is enabled by the use of Zn(TMP)2 as base and Zn(OTf)2 as an additive. The resulting alkylzinc species can be intercepted by electrophiles for tandem C–X and C–O bond formation.

Keywords: anionic cyclization; cyclization; mediated anionic; unstabilized ketone; zinc mediated; cyclization unstabilized

Journal Title: Tetrahedron
Year Published: 2020

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