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

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.