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

submitted on 21.08.2019, 02:33 and posted on 21.08.2019, 18:38 by Austin Gallagher, Huan Tian, Osmar A. Torres-Herrera, Shuai Yin, Anxin Xie, Daniel M. Lange, Jerica K. Wilson, Louis G. Mueller, Michael R. Gau, Patrick J. Carroll, Dionicio Martinez Solorio
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.


Email Address of Submitting Author


Drexel University


United States

ORCID For Submitting Author


Declaration of Conflict of Interest

The authors declare no competing financial interest.