Synthetic Method for 2,2'-Disubstituted Fluorinated Binaphthyl Derivatives and Application as Chiral Source in Design of Chiral Mono-Phosphoric Acid Catalyst

Norie Momiyama, Hiroshi Okamoto, Masahiro Shimizu, Masahiro Terada

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A practical synthetic method for 2,2'-disubstituted fluorinated binaphthyl derivatives was achieved using magnesium bis(2,2,6,6-tetramethylpiperamide) [Mg(TMP)2], prepared from LiTMP (2 equiv) and MgBr2 (1 equiv), which allows for access to a variety of fluorinated binaphthyl compounds. The utility of the fluorinated binaphthyl backbone was evaluated in F10BINOL derived chiral mono-phosphoric acid (R)-19 as the chiral Brønsted acid catalyst. The catalyst (R)-19 performs exceptionally well in the catalytic enantioselective imino-ene reaction, demonstrating the potential of a fluorinated binaphthyl framework. Chirality 27:464-475, 2015.

Original languageEnglish
Pages (from-to)464-475
Number of pages12
JournalChirality
Volume27
Issue number8
DOIs
Publication statusPublished - 2015 Aug 1

Keywords

  • axial chirality
  • chiral Brønsted acid
  • chiral phosphoric acid
  • fluorinated binaphthyl
  • organocatalyst

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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