Access to Highly Functionalized Cyclopentenones via Diastereoselective Pauson Khand Reaction of Siloxy-Tethered 1,7-Enynes
2019
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.
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