Diastereoselective reaction of a 2-nitroenamine with an excess of grignard reagent

Abstract

Nitroenamine 1 reacts with four equivalents of Grignard reagents to yield hydroxylamines 8–10 after hydrolysis. In the case of 8 and 10 this reaction is highly diastereoselective (Scheme). 1H-NMR signal assignments of imidazolidine 3 by NOE result in the relative configurations (Scheme) for the preferred diastereomers of 2 and 4.