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Org Lett. 2011 Aug 5;13(15):4076-9. doi: 10.1021/ol201581c. Epub 2011 Jul 6.

Regioselective carbon-carbon bond cleavage in the oxidation of cyclopropenylcarbinols.

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  • 1Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000 Israel.

Abstract

The strained double bond of cyclopropenylcarbinols undergoes a facile oxidation reaction to lead to unsaturated carbonyl derivatives. The distribution of the formed products depends on the relative stability of carbon-centered radical species, and the Sharpless kinetic resolution leads to enantiomerically pure Baylis-Hillman enal adducts.

© 2011 American Chemical Society

PMID:
21732683
[PubMed]
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