Carbamoyl Anion Addition to Nitrones

Abstract

The addition of carbamoyl anions derived from <i>N</i>,<i>N</i>-disubstituted formamides and LDA to <i>N</i>-<i>tert</i>-butyl nitrones is described. The reaction was demonstrated with a variety of formamides and nitrones and provided a direct route to α-(<i>N</i>-hydroxy)­amino amides. The use of a <i>tert</i>-leucinol derived chiral auxiliary on the nitrone provided products in good diastereoselectivity. Derivatization of the products by <i>tert</i>-butyl deprotection or <i>N</i>-deoxygenation was demonstrated