Enantioselective catalyzed synthetic processes are ubiquitous for the preparation of nonracemic chiral organic compounds. In most cases, new catalysts are only evaluated in standard substrates eluding systematically challenging substrates that would yield to interesting chiral synthons.<br/>In this communication we will present our latest investigations for the Pd-catalyzed decarboxylative protonation of α-aryl-α-amido allyl esters and for the development of a general synthesis of 6,6-disubstituted pentafulvenes bearing chiral pendant hydroxy groups via cascade reactivity using commercially available proline-based organocatalysts. The former reaction led to the formation of oxindoles, which are endogenous aromatic organic compounds that are found in the tissues and body fluids of mammals. The oxindole skeleton is also present in many natural products with antiviral, antibacterial and anticarcinogenic effects. The latter represents a challenge because there is a complete complete lack of effective stereoselective syntheses of pentafulvenes. Nevertheless pentafulvenes remain a commonly used compound class. Frequent applications include: cycloadditions to generate complex, polycyclic scaffolds and their use as intermediates in the synthesis of substituted (sometimes chiral) cyclopentadienyl derivatives via nucleophilic addition to the exocyclic C=C bond as a route to (asymmetric) cyclopentadiene units.

New approaches for the preparation of elusive chiral synthons

256th National Meeting (2018)

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