A highly diastereoselective [2,3]-sigmatropic N,O rearrangement
Bull SD., Davies SG., Jones S., Ouzman JVA., Price AJ., Watkin DJ.
Lithium (E)-N-benzyl-O-(4-methoxy-4-phenylbut-2-enyl)-hydroxylamide undergoes a highly diastereoselective rearrangement via a chelated transition state, to afford after reduction, syn-3-benzylamino-4-methoxy-4-phenylbut-1-ene as a single diastereoisomer.