Enantioselective, electrocatalytic lactonization of methyl-substituted diols on a TEMPO-modified graphite felt electrode in the presence of (-)-sparteine

Yoshinori Yanagisawa, Yoshitomo Kashiwagi, Futoshi Kurashima, Jun Ichi Anzai, Tetsuo Osa, James M. Bobbitt

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

A TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxyl)-modified graphite felt electrode afforded enantioselective, electrocatalytic lactonized products of (S)-(-)-3,4,5,6-tetrahydro-4-melhyl-2-pyranone, (S)-(-)-4,5-dihydro-4-methyl-2(3H)-furanone and (S)-(-)-4,5-dihydro-5-methyl-2(3H)-furanone from 3-methylpentane-1,5-diol, (S)-(-)-2-methylbutane-1,4-diol and racemic pentane-1,4-diol, respectively, in enantiomeric excess more than 95%, in the presence of (-)-sparteine in acetonitrile. The current efficiency and isolated yield of former two lactones were more than 90%.

Original languageEnglish
Pages (from-to)1043-1044
Number of pages2
JournalChemistry Letters
Issue number12
DOIs
Publication statusPublished - 1996 Jan 1

ASJC Scopus subject areas

  • Chemistry(all)

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