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Activated sulfahydantoin as Boc-glycine enolate equivalent: highly diastereoselective alpha-hydroxyalkylation and application to the synthesis of aldopentonate analogues
Journal article   Peer reviewed

Activated sulfahydantoin as Boc-glycine enolate equivalent: highly diastereoselective alpha-hydroxyalkylation and application to the synthesis of aldopentonate analogues

Djamel Bouchouk, Evelina Colacino, Loic Toupet, Nouredine Aouf, Jean Martinez and Georges Dewynter
Tetrahedron Letters, Vol.50, pp.1100-1104
2009

Abstract

Aldol reaction C-C activation Sulfahydantoin Diastereoselectivity transSulfamoylation Polyoxamic acid analogues ß-hydroxy alpha-aminoacids Rearrangement. Rearrangement
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 methdology allowed the one-pot preparation of constrained analogues of polyoxamic
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