Rhodium-catalyzed hydroacylation is an atom economical method for preparing ketones from readily available aldehyde and olefin precursors. While many hydroacylations leading to unsymmetrical ketones have been developed, most rely on the use of chelating aldehydes in order to avoid competing aldehyde decarbonylation.  In this presentation, a strategy will be described for achieving hydroacylation of simple aldehydes. Coupling these substrates with olefins that bear an anionic directing group results in high levels of reactivity and regioselectivity for a-branched ketone products. The reaction development and scope, a mechanistic study, and applications to the synthesis of small natural products will be presented.

Hydroacylation of aldehydes with olefins bearing anionic directing groups

246th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.