Cyclization of α-Diazo Esters Triggered by Oxidation: A Facile Preparation of 5-Aryl-2,3-dihydrofuran-4-carboxylates

Hideaki Kondo, Hiroyuki Yamakoshi, Ayaka Kimura, Seiichi Nakamura

Research output: Contribution to journalArticlepeer-review

Abstract

A method for the preparation of 5-aryl-2,3-dihydrofuran-4-carboxylates has been developed. Exposure of 4-(arylmethyl)oxy-2-diazobutyrates to 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) effected oxidative generation of oxocarbenium intermediates, which underwent intramolecular attack of the diazo carbon atom and subsequent β-elimination to give 5-aryl-2,3-dihydrofurancarboxylates in modest to good yields. In particular, tertiary arylmethyl ethers offer the advantages of enhanced reactivity toward DDQ and higher product yields due to a Thorpe−Ingold effect. To demonstrate the synthetic utility of the cyclization reaction, selective transformations of an aromatization-prone dihydrofuran product are also described.

Original languageEnglish
Pages (from-to)5646-5649
Number of pages4
JournalChemistrySelect
Volume2
Issue number20
DOIs
Publication statusPublished - 2017 Jul 11
Externally publishedYes

Keywords

  • cyclization
  • diazo compounds
  • dihydrofuran
  • oxidation
  • quinones

ASJC Scopus subject areas

  • Chemistry(all)

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