A selective Heck-arylation of a chiral highly functionalized cyclohexadiene, easily obtained by biocatalytic oxidation of benzoic acid is demonstrated. Interestingly, the reaction effects a 1,3-chirality transfer, yielding a non-conjugated diene. The mechanism and selectivity of the reaction were investigated using DFT calculations.<br/>A palladium catalyzed cascade reaction is triggered when a benzaldehyde moiety is present in the <i>ortho </i>position of the aryl halide coupling partner. In this way, a highly functionalized tetrahydrofluorenone skeleton, containing two new stereocenters, is obtained as a single diastereomer. This cascade reaction is also under investigation as a key step in the synthesis of a natural product synthesis.

Palladium catalyzed stereospecific arylation of biocatalytically derived dienes: Chirality transfer via a Heck-type mechanism

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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