Ring-Closing Metathesis Reactions of Bis(enynes): Selectivity and Surprises.

A study of the ring-closing metathesis reactions of two bis(enynes) is presented. These substrates, which contain two alkenes and two alkynes, as well as a resident stereocenter, can potentially generate metathesis products resulting from many reaction pathways. In this contribution we present our results on these reactions, show how small changes in reaction conditions can lead to different product ratios, and attempt to provide a rationale for the outcomes.