Asymmetric construction of binaphthyl by the chiral diether-mediated conjugate addition of naphthyllithium to naphthalenecarboxylic acid 2,6-di-t-butyl-4-methoxyphenyl ester

Mitsuru Shindo, Yasutomo Yamamoto, Ken Ichi Yamada, Kiyoshi Tomioka

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Two ways for the synthesis of binaphthyl were examined based on a chiral ligand-mediated asymmetric conjugate addition of 1-naphthyllithium to naththalene-2-carboxylic acid 2,6-di-t-butyl-4-methoxyphenyl esters. The one pot method by conjugate addition-elimination gave a relatively higher enantioselectivity than the two step synthesis based on addition and subsequent oxidative aromatization.

Original languageEnglish
Pages (from-to)752-754
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume57
Issue number7
DOIs
Publication statusPublished - Jul 1 2009

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Carboxylic Acids
Esters
Ligands
Aromatization
Enantioselectivity
naphthyllithium
naphthalenecarboxylic acid 2,6-di-t-butyl-4-methoxyphenyl ester

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

Asymmetric construction of binaphthyl by the chiral diether-mediated conjugate addition of naphthyllithium to naphthalenecarboxylic acid 2,6-di-t-butyl-4-methoxyphenyl ester. / Shindo, Mitsuru; Yamamoto, Yasutomo; Yamada, Ken Ichi; Tomioka, Kiyoshi.

In: Chemical and Pharmaceutical Bulletin, Vol. 57, No. 7, 01.07.2009, p. 752-754.

Research output: Contribution to journalArticle

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