Asymmetric synthesis of axially chiral 1,1'-biphenyl-2-carboxylates via nucleophilic aromatic substitution on 2-menthoxybenzoates by aryl grignard reagents

Tetsutaro Hattori, Nobuyuki Koike, Sotaro Miyano

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31 Citations (Scopus)

Abstract

A practical method is presented for an asymmetric synthesis of axially chiral 1,1′-biphenyl-2carboxylates via the ester-assisted nucleophilic aromatic substitution reaction. Thus, upon treatment of 2-tert-butylphenyl 2-[(-)-menthoxy]benzoates with an aryl Grignard reagent, chirality of the leaving (-)-menthoxy group is transferred to the newly formed biphenyl linkage with up to 94% optical yield.

Original languageEnglish
Pages (from-to)2273-2282
Number of pages10
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number16
DOIs
Publication statusPublished - 1994

ASJC Scopus subject areas

  • Chemistry(all)

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