Z-selective cross metathesis with ruthenium catalysts: synthetic applications and mechanistic implications

Abstract

Olefin cross metathesis is a particularly powerful transformation that has been exploited extensively for the formation of complex products. Until recently, however, constructing Z-olefins using this methodology was not possible. With the discovery and development of three families of ruthenium-based Z-selective catalysts, the formation of Z-olefins using metathesis is now not only possible but becoming increasingly prevalent in the literature. In particular, ruthenium complexes containing cyclometalated NHC architectures developed in our group have been shown to catalyze various cross metathesis reactions with high activity and, in most cases, near perfect selectivity for the Z-isomer. The types of cross metathesis reactions investigated thus far are presented here and explored in depth.

Keywords: Z-alkenes; cross metathesis; natural products; olefin metathesis.