Asymmetric ring-closing metathesis with a twist

Angew Chem Int Ed Engl. 2009;48(12):2085-9. doi: 10.1002/anie.200806254.

Abstract

A double flip! The catalyst shown, with a molybdenum stereocenter and monodentate ligands (Si = SitBuMe(2)), promotes asymmetric ring-closing metathesis of a broad range of substrates. Its unprecedented activity originates from its structural fluxionality, which enables double inversion at the metal center in the course of a single catalytic cycle. The catalyst passed the test in a metathesis reaction en route to (+)-quebrachamine (see scheme).