Access to Highly Functionalized Cyclopentenones via Diastereoselective Pauson Khand Reaction of Siloxy-Tethered 1,7-Enynes

21 August 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


A diastereoselective Co2(CO)8-mediated Pauson-Khand reaction (PKR) of siloxy-tethered 1,7-enynes for the synthesis of cyclopentaoxasilinones has been developed. This transformation can be performed on a multi-gram scale and is characterized by broad substrate scope, functional group compatibility, and high chemo- and diastereoselectivity. Oxidation of the resulting cyclopentaoxasilinones delivers stereoenriched β-alkylated cyclopentenones, which are inaccessible by intermolecular PKRs. This research provides a practical solution to the challenges associated with the classical intermolecular PKR.


Pauson-Khand reactions
Synthetic methods-
diastereoselective access
Gram scale reactions
Broad Substrate Scope
Cyclopentenone Synthesis

Supplementary materials

Si-O Tethered PKR SI final draft


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