A new strategy for the preparation of heterocyclic β-amino esters: orthogonally protected β-amino esters with a piperidine skeleton

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28 Citations (Scopus)

Abstract

A simple strategy is presented for the introduction of a nitrogen atom into the carbocycle of an aminocyclopentenecarboxylic ester via dihydroxylation of the olefinic bond, followed by NaIO4-mediated cleavage of the diol intermediate and ring expansion, resulting in new regioisomeric 3-amino-4-piperidinecarboxylic acid derivatives. This method permits the preparation of amino esters with a piperidine skeleton in enantiomerically pure form.

Original languageEnglish
Pages (from-to)339-342
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number2
DOIs
Publication statusPublished - Jan 7 2008

Keywords

  • Cyclic β-amino acids
  • Dihydroxylation
  • Enzymatic resolution
  • Piperidine
  • Ring closure

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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