Electroauxiliary-assisted sequential introduction of organic groups on the α-carbons of nitrogen

Seiji Suga, Mitsuru Watanabe, Chun Hong Song, Jun Ichi Yoshida

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A method for sequential introduction of two organic groups on the same or the different α-carbons of nitrogen has been developed based on a combination of the concept of electroauxiliary and the cation pool method. Selective introduction of two carbon nucleophiles into 2,5- or 2,2-position of pyrrolidine has been accomplished via sequential electrochemical oxidation of pyrrolidine derivatives containing two silyl groups as the electroauxiliaries. Introduction of two carbon nucleophiles into 2,6-position of piperidine was also successful. The products having two olefinic groups were effectively converted to nitrogen-containing spiro compounds using ring closing metathesis, and an application to formal synthesis of cephalotaxine was also carried out. These results clearly illustrate the synthetic utility and potential of the present approach, and open a new aspect of the synthesis of nitrogen-containing compounds.

Original languageEnglish
Pages (from-to)672-679
Number of pages8
JournalElectrochemistry
Volume74
Issue number8
DOIs
Publication statusPublished - Aug 2006
Externally publishedYes

Keywords

  • Cation Pool Method
  • Electroauxiliary
  • Electrooxidation
  • Piperidine
  • Pyrrolidine
  • Spiro Compound

ASJC Scopus subject areas

  • Electrochemistry

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