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J Am Chem Soc. 2006 Apr 12;128(14):4576-7.

[3,3]-rearrangements of phosphonium ylides.

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  • 1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.


Allylic phosphonium ylides are readily generated by the combination of an allylic alcohol, a carbene, and a chlorophosphite. Here we demonstrate that these intermediates undergo a thermal [3,3]-rearrangement to provide single isomers of homoallylic phosphonates in good to excellent yields. This new reaction manifold for phosphorus ylides is tolerant of a range of substitution patterns on the reactants and provides access to structurally complex intermediates for the synthesis of enzyme inhibitors, aminophosphonic acids, and natural products.

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