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

作者：Bouchouk Djamel; Colacino Evelina; Toupet Loic; Aouf Noureddine; Martinez Jean; Dewynter Georges^*

来源：Tetrahedron Letters, 2009, 50(10): 1100-1104.

DOI：10.1016/j.tetlet.2008.12.070

• Aldol reaction
• C-C activation
• Sulfahydantoin
• Diastereoselectivity
• transSulfamoylation
• Polyoxamic acid analogues
• beta-hydroxy alpha-aminoacids
• 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 methodology allowed the one-pot preparation of constrained analogues of polyoxamic acid.

• 出版日期2009-3-11