The development of new methods for the construction of stereochemically pure compounds is an active area of investigation in modern synthetic organic chemistry. In this regard, the synthesis of geometrically defined tetrasubstituted olefins is a highly challenging endeavour. Nevertheless, this ubiquitous functional group is an important motif in pharmaceutical agents and materials research, where the geometry of the alkene often plays a critical role in the activity and properties of a specific compound. Despite the challenges associated with traditional olefination methods, many modern methods continue to employ the same general technique that involves the <i>de novo</i> installation of the carbon-carbon double bond. This strategy requires stereochemical control of the substituents within the newly formed olefin, a challenge that is often difficult to overcome and thus hampers the synthetic utility of these processes. Herein, we will describe a new approach that can prepare geometrically defined olefins through a novel dynamic kinetic resolution of olefin mixtures with excellent selectivity and broad substrate scope. Moreover, we will outline the mechanistic origin of stereocontrol, which was delineated using DFT calculations.

Dynamic kinetic resolution of tetrasubstituted olefins

255th National Meeting (2018)

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