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New developments in nucleophilic additions to nitrones

Authors
Journal
Comptes Rendus Chimie
1631-0748
Publisher
Elsevier
Publication Date
Volume
8
Issue
5
Identifiers
DOI: 10.1016/j.crci.2005.02.013
Keywords
  • Nitrones
  • Hydroxylamines
  • Nucleophilic Additions
  • Aminoalcohols
  • Aminoacids
  • Nucleosides
  • Additions Nucléophiles
  • Aminoalcools
  • Aminoacides
  • Nucléosides
Disciplines
  • Biology

Abstract

Abstract Nucleophilic addition reactions to chiral non-racemic nitrones have gained considerable attention in organic synthesis during the last years as methods for accessing hydroxylamines that can be further transformed in important nitrogen-containing compounds. This review covers significant advances made in the use of nitrones derived from sugars and aminoacids as starting materials for the synthesis of biologically interesting compounds including aminoacids, aminoalcohols and nucleoside analogues. Considerable emphasis has been placed on the stereocontrol of the studied processes. The reaction can be completely stereocontrolled by the use of the appropriate Lewis acid as precomplexing agent in the case of alpha-alkoxy nitrones. On the other hand, nucleophilic additions to alpha amino nitrones are only sterecontrolled by protecting differentially the amino group. To cite this article: P. Merino, C. R. Chimie 8 (2005) .

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