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

preprint
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.

History

Email Address of Submitting Author

dionicio.s.martinez@drexel.edu

Institution

Drexel University

Country

United States

ORCID For Submitting Author

0000-0003-3658-2658

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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