Synthesis 2012; 44(16): 2567-2574
DOI: 10.1055/s-0032-1316548
paper
© Georg Thieme Verlag Stuttgart · New York

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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Publikationsverlauf

Received: 08. April 2012

Accepted after revision: 16. Mai 2012

Publikationsdatum:
02. Juli 2012 (online)


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.

Supporting Information