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

Organic Letters
Xiaoyu ChenPhilip Wai Hong Chan

Abstract

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.

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Citations

Apr 11, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Yongjia LinYuanzhi Xia
Mar 5, 2019·Chemistry : a European Journal·Vanessa ClausA Stephen K Hashmi

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