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Cocatalyst-controlled divergent cascade cycloaddition reaction of arylalkynols and dioxopyrrolidienes: access to spiroketals and oxa-bridged eight-membered cyclic ethers

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Abstract

A cocatalyst-controlled divergent cascade cycloaddition reaction was developed for the synthesis of two different complex oxygen-containing heterocyclic compounds from arylalkynols and dioxopyrrolidienes in the presence of Au(I) catalyst. Using two different cocatalysts, Ni(OTf)2 and (rac)-phosphoric acid, two completely different products, spiroketals and oxa-bridged eight-membered cyclic ethers, were precisely constructed with high yields and good stereoselectivities, respectively. These methods feature simple and high efficiency, good chemoselectivity and mild conditions in one-pot.

Graphical abstract: Cocatalyst-controlled divergent cascade cycloaddition reaction of arylalkynols and dioxopyrrolidienes: access to spiroketals and oxa-bridged eight-membered cyclic ethers

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Article information


Submitted
17 Apr 2020
Accepted
20 May 2020
First published
21 May 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Cocatalyst-controlled divergent cascade cycloaddition reaction of arylalkynols and dioxopyrrolidienes: access to spiroketals and oxa-bridged eight-membered cyclic ethers

H. Wang, T. Zeng, X. Li, S. Wang, W. Xiao, L. Liu, W. Chang and J. Li, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00464B

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