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Issue 32, 2018
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Regioselective addition of phosphites to acyl cyclopropanes and following rearrangements: a facile access to enol phosphates

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Abstract

An inorganic base-promoted domino reaction with organophosphites and acyl cyclopropane derivatives is developed and proved to provide an efficient access to functionalized enol phosphates. Unlike the well-known Perkow reaction, which employs trialkyl phosphite as the nucleophile, dialkyl phosphite is the key to the success of our transformation. This method is compatible with a series of dialkyl phosphites and acyl cyclopropanes possessing electron-withdrawing substituents, and an array of functionalized enol phosphates are successfully prepared. Based on the results of isotope-labeling and control experiments, this transformation is presumably initiated by the deprotonation of dialkyl phosphite and the following nucleophilic addition/anion shift/ring opening sequence leads to the formation of enol phosphates. Both the strain release of a three-membered ring and the formation of a relatively stable anion are indispensable driving forces for this process.

Graphical abstract: Regioselective addition of phosphites to acyl cyclopropanes and following rearrangements: a facile access to enol phosphates

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Publication details

The article was received on 29 Jun 2018, accepted on 24 Jul 2018 and first published on 25 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01533C
Citation: Org. Biomol. Chem., 2018,16, 5907-5912
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    Regioselective addition of phosphites to acyl cyclopropanes and following rearrangements: a facile access to enol phosphates

    H. Li, Y. Zhu, D. Lu and Y. Gong, Org. Biomol. Chem., 2018, 16, 5907
    DOI: 10.1039/C8OB01533C

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