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Gold-Catalyzed Formal [4 + 2] Cycloaddition of 5‑(Ethynylamino)pent-2-yn-1-yl Esters to 1,2,3,5-Tetrahydrobenzo[g]quinolines

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journal contribution
posted on 26.02.2018, 19:52 by Xiaoyu Chen, James Theodore Merrett, Philip Wai Hong Chan
A synthetic method to prepare 1,2,3,5-tetrahydrobenzo­[g]­quinolines efficiently that relies on gold­(I)-catalyzed cycloisomerization of 5-(ethynylamino)­pent-2-yn-1-yl esters at room temperature under atmospheric conditions is described. The proposed reaction mechanism presents a unique instance of an in situ formed allenic ester and gold keteniminium species to undergo a formal [4 + 2] cycloaddition pathway.