Multicomponent reactions of phosphines, diynedioates, and aryl aldehydes generated furans appending reactive phosphorus ylides through cumulated trienoates as key intermediates: A phosphine α-addition-δ-evolvement of an anion pathway

Jie Cheng Deng, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Multicomponent reactions of phosphines, diynedioates, and aryl aldehydes have been demonstrated, providing trisubstituted furans appending reactive phosphorus ylides, through cumulated trienoates as key intermediates. The proposed trienoate intermediates, 1,5-dipolar species formed via nucleophilic α-attack of phosphines toward diynedioates (α-addition-δ-evolvement of an anion, abbreviated αAδE), undergo addition to aryl aldehydes followed by 5-endo-dig cyclization, proton transfer, and resonance to give trisubstituted furans. Furthermore, the phosphorus ylides are oxidized to α-keto ester furans and utilized as Wittig reagents.

Original languageEnglish
Pages (from-to)5792-5795
Number of pages4
JournalOrganic Letters
Volume16
Issue number21
DOIs
StatePublished - 7 Nov 2014

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