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

  Institute for Materials Chemistry and Engineering, Kyushu University

• Yamamoto Yasutomo

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Yamada Ken-ichi

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Tomioka Kiyoshi

  Graduate School of Pharmaceutical Sciences, Kyoto University

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.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 57 (7), 752-754, 2009

  The Pharmaceutical Society of Japan

Keywords

• axial chirality
• central chirality
• asymmetric addition
• chiral ligand

Details

• CRID: 1390001204170324864
• NII Article ID: 130000124382
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.57.752
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 10264816
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I10264816
• Web Site: http://www.jstage.jst.go.jp/article/cpb/57/7/57_7_752/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed