Synthesis of orthogonally protected azepane β-amino ester enantiomers

Brigitta Kazi, L. Kiss, E. Forró, F. Fülöp

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

A simple and convenient route is presented for the preparation of regio- and stereoisomers of novel azepane β-amino esters, starting from bicyclic β-lactam isomers. The synthetic procedure consists of dihydroxylation of the olefinic bond of the alicyclic amino esters, followed by NaIO4-mediated cleavage of the diol intermediate and reductive ring closure, which furnishes novel regioisomeric 5-aminoazepane-4-carboxylate and 3-aminoazepane-4-carboxylates. This method also allows the preparation of amino esters with an azepane skeleton in enantiomerically pure form.

Original languageEnglish
Pages (from-to)82-85
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number1
DOIs
Publication statusPublished - Jan 6 2010

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Enantiomers
Esters
Lactams
Stereoisomerism
Skeleton
Isomers

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of orthogonally protected azepane β-amino ester enantiomers. / Kazi, Brigitta; Kiss, L.; Forró, E.; Fülöp, F.

In: Tetrahedron Letters, Vol. 51, No. 1, 06.01.2010, p. 82-85.

Research output: Contribution to journalArticle

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