Preparation of tert-alkyl azides from tertiary alcohols by way of benzoquinone-mediated oxidation-reduction condensation

Kiichi Kuroda, Nobuya Kaneko, Yujiro Hayashi, Teruaki Mukaiyama

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A novel method for the preparation of alkyl azides from alcohols by way of oxidation-reduction condensation is described. According to this reaction, the sterically hindered tert-alkyl phosphinites that are prepared from the corresponding alcohols are converted into tert-alkyl azides with almost complete inversions of their stereochemistries. On treatment with LiAlH4 the obtained alkyl azides are then successfully reduced to afford the corresponding amines in good yields, thus, a versatile method for the preparation of chiral amines from the corresponding chiral alcohols was established.

Original languageEnglish
Pages (from-to)1432-1433
Number of pages2
JournalChemistry Letters
Volume35
Issue number12
DOIs
Publication statusPublished - 2006 Dec 5
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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