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2020•European Journal of Organic ChemistryRequires access

Gold‐Catalyzed Sequential Cycloisomerization of 1,3,9‐Ene‐allene‐ynes to Fused Spirocarbocycles

Xianxiao Chen, Xiangxiang Ling, Di An, Weidong Rao

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Abstract

An efficient synthetic method to prepare architecturally challenging spiro tetrahydro‐3H‐dicyclopenta[a,b]naphthalene derivatives from Au(I)‐catalyzed intramolecular sequential cycloisomerization of linear 1,3,9‐ene‐allene‐ynes is described. The proposed cycloisomerization pathway involves an initial gold‐catalyzed 1,3‐ene‐allene cycloisomerization, followed by a formal [4+2] cycloaddition to give fused spirocarbocyclic products containing a quaternary centre.

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What this paper is about

An efficient synthetic method to prepare architecturally challenging spiro tetrahydro‐3H‐dicyclopenta[a,b]naphthalene derivatives from Au(I)‐catalyzed intramolecular sequential cycloisomerization of linear 1,3,9‐ene‐allene‐ynes is described. The proposed cycloisomerization pathway involves an initial gold‐catalyzed 1,3‐ene‐allene cycloisomerization, followed by a formal [4+2] cycloaddition to give fused spirocarbocyclic products containing a quaternary centre.

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Available abstract

An efficient synthetic method to prepare architecturally challenging spiro tetrahydro‐3H‐dicyclopenta[a,b]naphthalene derivatives from Au(I)‐catalyzed intramolecular sequential cycloisomerization of linear 1,3,9‐ene‐allene‐ynes is described. The proposed cycloisomerization pathway involves an initial gold‐catalyzed 1,3‐ene‐allene cycloisomerization, followed by a formal [4+2] cycloaddition to give fused spirocarbocyclic products containing a quaternary centre.

Key concepts: Cycloisomerization, Allene, Chemistry, Cycloaddition, Ene reaction, Intramolecular force, Catalysis, Stereochemistry

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