Silver(I)-Mediated Cascade Reaction of 2-(1-Alkynyl)-2-alken-1-ones with 2-Naphthols

Organic Letters
Zhanhuan LiHongjun Ren

Abstract

An efficient cascade reaction of 2-(1-alkynyl)-2-alken-1-ones with 2-naphthols promoted by silver trifluoroacetate is disclosed, providing an expeditious access to 1,2-dihydronaphtho[2,1-b]furans with moderate to good yields. This domino process involves highly regio- and diastereoselective sequential cyclization/nucleophilic addition/oxidative ring opening/oxa-Michael addition reactions to construct three new chemical bonds and one new five-membered ring. A gram-scale experiment and the preliminary results to develop an asymmetric variant are also presented to show the practicality and potential of the current reaction.

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Citations

Oct 1, 2020·Organic & Biomolecular Chemistry·Xiaoze BaoHong Wang

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