Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol

Caroline Aciro, Stephen G. Davies, Paul M. Roberts, Angela J. Russell, Andrew D. Smith, James E. Thomson

Research output: Contribution to journalArticlepeer-review

49 Citations (Scopus)

Abstract

The ammonium-directed, metal-free oxidation of 3-(N,N-dibenzylamino)cyclohex-1-ene with mCPBA in the presence of either trichloroacetic acid or tosic acid has been used as the key step to facilitate the synthesis of all the diastereoisomers of 3-aminocyclohexane-1,2-diol, in >98% de in each case.

Original languageEnglish
Pages (from-to)3762-3770
Number of pages9
JournalOrganic & Biomolecular Chemistry
Volume6
Issue number20
DOIs
Publication statusPublished - 21 Oct 2008

Keywords

  • JASPINE-B PACHASTRISSAMINE
  • D-LYXO-PHYTOSPHINGOSINE
  • VICINAL AMINO-ALCOHOLS
  • ASYMMETRIC-SYNTHESIS
  • STEREOSELECTIVE EPOXIDATION
  • MECHANISMS
  • SALTS

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