Enantioselective Catalytic Oxidation of 1-Phenylethanol on a Chiral Nitroxyl Radical-terminated Self-assembled Monolayer Modified Electrode

Yoshitomo Kashiwagi, Kazumi Uchiyama, Futoshi Kurashima, Jun Ichi Anzai, Tetsuo Osa

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Thiol derivatized (6S,7R,10R)-4-amino-2,2,7-trimethyl-10-isopropyl-1-azaspiro[5.5]undecane-1- yloxyl was synthesized to modify the surface of a gold electrode with its self-assembled monolayer. This modified electrode showed symmetrical reversible redox wave at +0.62 V vs. Ag / AgCl, which originates from the electron transfer between the self-assembled monolayer and electrode. The modified electrode exhibited an enantioselective catalytic oxidation for chiral secondary alcohols ; (S)-(-)-1-phenylethanol was oxidized into the ketone more efficiently than (R)-(+)-1-phenylethanol.

Original languageEnglish
Pages (from-to)900-902
Number of pages3
JournalElectrochemistry
Volume67
Issue number9
DOIs
Publication statusPublished - 1999 Sep

Keywords

  • Chiral Nitroxyl Radical
  • Enatioselective Electrocatalytic Oxidation
  • Self-assembled Monolayer

ASJC Scopus subject areas

  • Electrochemistry

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