Easy Access to Acetal-Spiroacetal-Enol Ethers by Tandem Dearomatization of a Furan Ring and Acetalization

Biao-Lin Yin; Jin-Qiang Lai; Li Huang; Xiao-Yu Zhang; Fang-Hua Ji

doi:10.1055/s-0032-1316548

Synthesis, Table of Contents

Synthesis 2012; 44(16): 2567-2574
DOI: 10.1055/s-0032-1316548

paper

Easy Access to Acetal-Spiroacetal-Enol Ethers by Tandem Dearomatization of a Furan Ring and Acetalization

Biao-Lin Yin*

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China, Fax: 0086(20)87113735 Email: blyin@scut.edu.cn

,

Jin-Qiang Lai

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China, Fax: 0086(20)87113735 Email: blyin@scut.edu.cn

,

Li Huang

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China, Fax: 0086(20)87113735 Email: blyin@scut.edu.cn

,

Xiao-Yu Zhang

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China, Fax: 0086(20)87113735 Email: blyin@scut.edu.cn

,

Fang-Hua Ji

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. of China, Fax: 0086(20)87113735 Email: blyin@scut.edu.cn

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Abstract

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Abstract

A range of structurally novel acetal-spiroacetal-enol ethers were readily synthesized from 3-[5-(methoxymethyl)-2-furyl]propionaldehydes by dearomatization to form carbocations that were trapped intramolecularly by the formyl group with subsequent acetalization.

Key words

enols - ethers - heterocycles - furans - carbocations

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References

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