Gold-catalyzed heterocycle synthesis using homopropargylic ethers as latent electrophiles

Organic Letters
Hyung Hoon Jung, Paul E Floreancig

Abstract

[reaction: see text] Homopropargylic ethers with pendent nucleophiles, when subjected to Au catalysts in aqueous solvent, provide heterocyclic ketones. The reactions are efficient, tolerant of functionality and ambient atmosphere, and operationally simple. Diastereoselectivity can be predicted on the basis of product thermodynamics. This process demonstrates the viability of homopropargylic ethers to serve as latent electrophiles that can be unraveled under highly selective conditions to promote heterocycle formation through nucleophilic additions to alpha,beta-unsaturated ketones.

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Citations

Sep 20, 2008·Chemical Communications : Chem Comm·Gregory W O'Neil, Alois Fürstner
Feb 13, 2014·Chemistry : a European Journal·Manish KumarBo Xu
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Feb 28, 2015·Chemical Reviews·Liangbin HuangLukas J Gooßen
Apr 7, 2015·Chemical Reviews·Ruth Dorel, Antonio M Echavarren

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