A long-standing challenge to synthetic organic chemists is the ability to forge stereocenters in substructures that do not contain pre-installed functional groups. In this regard, we have recently developed a catalytic and enantioselective intermolecular Heck-type reaction of multi-substituted alkenyl alcohols allowing for the installation of various groups (aryl and alkenyl) that are remote from the alcohol. The reported methods allow direct access to β-, γ-, δ-, e- or ζ aryl carbonyl functionalized compounds, as the unsaturation of the alkene is relayed to the alcohol resulting in the formation of a carbonyl. This is accomplished through a series of migratory insertion/ β-hydride elmination events, which allows the Pd-center to chain walk to the prefunctionalized site in the molecule. In this lecture, the design, development, scope, and mechanistic analysis will be discussed of this reaction as well as new findings guided by the mechansitic insight garnered in our studies.

Award Address (ACS Award for Creative Work in Synthetic Organic Chemistry sponsored by MilliporeSigma). Enantioselective formation of remote chiral centers through Pd-catalyzed alkene functionalization

253rd National Meeting (2017)

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