The Pauson-Khand reaction (PKR) is a prominent transformation for the synthesis of cyclopentenones. In particular, the intramolecular variant has been widely exploited. Although notable advances have been made, the intermolecular PKR remains restricted to strained, cyclic, or symmetrical olefins. Problems arise from alkene regioselectivity, and mixtures of cyclopentenones are often observed. A tactic to define the regioselectivity is to use a removable tether, preferably one that allows further functionalization. Our research group is currently developing silicon and boron-containing tethers in the PKR reaction because of the excellent potential for post-cyclization manipulation. This talk will focus on our efforts that have now led to the successful development of the first diastereoselective Co<sub>2</sub>(CO)<sub>8</sub>-mediated Pauson−Khand reaction (PKR) of siloxy-tethered 1,7-enynes for the synthesis of cyclopentaoxasilinones. Oxidation of the resulting cyclopentaoxasilinones delivers densely functionalized, stereoenriched β-alkylated cyclopentenones, which are inaccessible by intermolecular PKRs. Preliminary results towards the development of a catalytic variant, future directions, and advantages/disadvantages of boron vs. silicon tethers in the PKR will also be discussed.

Development of silicon and boron tethered Pauson-Khand reactions

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.