Conversion of tertiary alcohols to tert-alkyl azides by way of quinone-mediated oxidation-reduction condensation using alkyl diphenylphosphinites

Kiichi Kuroda, Yujiro Hayashi, Teruaki Mukaiyama

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

A novel method for the preparation of alkyl azides from alcohols by way of oxidation-reduction condensation is described. In this reaction, the sterically-hindered tert-alkyl phosphinites that are prepared from the corresponding alcohols are converted into tert-alkyl azides with almost complete inversion of their stereochemistry: the obtained alkyl azides are then successfully reduced to afford the corresponding amines on treatment with LiAlH4, thus, a versatile method for the preparation of chiral amines from the corresponding chiral alcohols is established.

Original languageEnglish
Pages (from-to)6358-6364
Number of pages7
JournalTetrahedron
Volume63
Issue number27
DOIs
Publication statusPublished - 2007 Jul 2
Externally publishedYes

Keywords

  • Alkyl diphenylphosphinite
  • Oxidation-reduction condensation
  • Quinone
  • Trimethylsilyl azide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Conversion of tertiary alcohols to tert-alkyl azides by way of quinone-mediated oxidation-reduction condensation using alkyl diphenylphosphinites'. Together they form a unique fingerprint.

  • Cite this