New developments in nucleophilic additions to nitrones

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. (c) 2005 Academie des sciences. Published by Elsevier SAS. All rights reserved.