A ring-closing metathesis approach to cyclic alpha,beta-dehydroamino acids

A comprehensive study on the synthesis and ring-closing metathesis (RCM) of alpha,beta-dehydroamino acids is described. This sequence has led to the formation of a range of biologically relevant functionalized nitrogen heterocycles. The incorporation of chiral building blocks in the RCM precursors eventually resulted in the formation of optically active 4-substituted cyclic dehydroamino acids. In addition, olefin isornerization under metathesis conditions was observed for a number of compounds, which could be successfully inhibited either by the introduction of allylic substituents or by the addition of a ruthenium hydride scavenger.