Stereocontrolled transformation of cyclohexene β-amino esters into syn- or anti-difunctionalized acyclic β2,3-amino acid derivatives

Maria Cherepanova, Loránd Kiss, Ferenc Fülöp

Research output: Article

13 Citations (Scopus)

Abstract

A stereocontrolled approach to functionalized acyclic β2,3- amino acid derivatives was accomplished from cis- or trans-2- aminocyclohexenecarboxylates derived from bicyclic β-lactam regioisomers. The transformations were based on oxidative ring cleavage through the ring C-C double bond of the cyclohexene β-amino esters, followed by functionalization of the dialdehyde intermediates with different phosphoranes. This stereospecific and stereocontrolled procedure was applied to the synthesis of acylic β2,3-amino acid derivatives functionalized with ester, nitrile, keto, alkyl or arylalkyl groups.

Original languageEnglish
Pages (from-to)2515-2522
Number of pages8
JournalTetrahedron
Volume70
Issue number15
DOIs
Publication statusPublished - ápr. 15 2014

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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