Sc(OTf)3-mediated 1,3-dipolar cycloaddition-ring cleavage-rearrangement: a highly stereoselective access to Z-ß-enaminonitriles.

ABSTRACT

A novel and highly stereoselective synthesis of Z-ß-enaminonitriles from azides and α,ß-unsaturated nitriles is reported. The reaction proceeds via a 1,3-dipolar cycloaddition-ring cleavage-rearrangement cascade mediated by a catalytic amount of Sc(OTf)3. A plausible reaction mechanism for this process is depicted.