N-heterocyclic carbenes (NHCs) have become ubiquitous in olefin metathesis, in both academic and industrial research environments. They owe this popularity to their remarkable aptitude in generating more stable, yet extremely reactive ruthenium catalysts. Thanks to pioneering reports by Grubbs and Hoveyda, a number of Ru-complexes featuring chiral diaminocarbene ligands have also been used with varying successes in asymmetric ring-opening cross-metathesis (AROCM) and ring-closing metathesis (ARCM).<br/><br/>In 2007, Grubbs and Bertrand demonstrated that cyclic (alkyl)(amino) carbenes (CAACs), a class of very ambiphilic carbenes, could compete with NHCs’s in ethenolysis processes reaching up to 340000 TON. Curious to see if their unique properties could be harnessed in asymmetric transformations, we sought to develop a new class of optically pure cyclic(alkyl)(amino)carbenes (CAACs). Herein we will discuss the preparation and reactivity of their ruthenium-complexes in asymmetric olefin metathesis processes.

Optically pure cyclic(alkyl)(amino)carbene (CAAC) ruthenium-complexes in asymmetric olefin metathesis

ACS Spring 2022

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