|
|||||
|
|
Activated sulfahydantoin as Boc-glycine enolate equivalent: highly diastereoselective α-hydroxyalkylation and application to the synthesis of aldopentonate analogues |
|
| Authors: | Djamel Bouchouk Evelina Colacino Noureddine Aouf Georges Dewynter |
| Institution: | a Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS-UMI-UMII, Groupe Synthèse Asymétrique et Aminoacides, Université de Montpellier 2, place E. Bataillon 34095 Montpellier cedex 5, France b LCOA Groupe de Chimie Bio-Organique, Université Badji Mokhatar, Annaba, Algeria c Groupe Matière Condensée et Matériaux, UMR 6626, Université de Rennes I, Campus de Beaulieu 35042 Rennes Cedex, France |
| Abstract: | N-Boc-activated sulfahydantoin can be seen as glycine enolate equivalent. It appeared as a convenient starting material for the stereocontrolled preparation of threonine homologues through an alkaline syn aldolization involving a Boc migration. The methodology allowed the one-pot preparation of constrained analogues of polyoxamic acid. |
| Keywords: | Aldol reaction C-C activation Sulfahydantoin Diastereoselectivity transSulfamoylation Polyoxamic acid analogues β-hydroxy α-aminoacids Rearrangement |
| 本文献已被 ScienceDirect 等数据库收录！ | |