Ester-mediated nucleophilic aromatic substitution of 2,3-alkylidenedioxybenzoic esters by aryl lithium reagents

Nobuyuki Koike, Tetsutaro Hattori, Ayanobu Takeda, Yoshikazu Okaishi, Sotaro Miyano

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

Treatment of 2,6-di-tert-butyl-4-methylphenyl 2,3-methylenedioxybenzoate with several aryllithium reagents in diethyl ether at 0°C affords 6-hydroxy-1,1′-biphenyl-2-carboxylates in good to excellent yields. Reaction of an (S)-(-)-2,3-ethylidenedioxybenzoic ester with 2-methoxy-4,6-dimethylphenyllithium induces R axial twist with not less than 81% diastereoselectivity in the biphenyl coupling.

Original languageEnglish
Pages (from-to)641-642
Number of pages2
JournalChemistry Letters
Issue number7
DOIs
Publication statusPublished - 1997 Jan 1

ASJC Scopus subject areas

  • Chemistry(all)

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