A de Novo stereocontrolled approach to syn- and anti-disubstituted acyclic β2,3-amino acid enantiomers

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The stereocontrolled syntheses of functionalized acyclic β2,3-amino acid derivatives in enantiomerically pure form were performed by starting from enantiopure cis- and trans-2-aminocyclopent-3- enecarboxylates, which were derived from a racemic bicyclic β-lactam. The synthetic strategy involves the stereoselective dihydroxylaton of the C-C double bond of the cyclopentene β-amino esters. The subsequent NaIO 4-mediated ring cleavage affords dialdehyde intermediates that undergo functionalization by a Wittig reaction. The stereocontrolled syntheses of functionalized acyclic β2,3-amino acid derivatives in enantiomerically pure form have been performed in five steps by starting from enantiopure cis- and trans-2-aminocyclopent-3-enecarboxylates, which were derived from a racemic bicyclic β-lactam.

Original languageEnglish
Pages (from-to)403-409
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number2
DOIs
Publication statusPublished - Jan 1 2014

Keywords

  • Amino acids
  • Diastereoselectivity
  • Kinetic resolution
  • Lactams
  • Synthetic methods
  • Wittig reactions

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'A de Novo stereocontrolled approach to syn- and anti-disubstituted acyclic β<sup>2,3</sup>-amino acid enantiomers'. Together they form a unique fingerprint.

  • Cite this