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Issue 44, 2017
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Stereoselective annulation between an allene, an alkene, and two nitrosoarenes to access bis(isoxazoliodine) derivatives

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Abstract

This work reports metal-free annulations between one allene, two nitrosoarenes and one electron-deficient alkene to afford bis(isoxazolidine) derivatives stereoselectively. This process involves an initial formation of isoxazolidin-4-imine oxides, followed by their dipolar [3 + 2]-cycloaddition with electron-deficient alkenes. To highlight the utility, the annulations of 5-alleneyl-1-enes with nitrosoarenes were also feasible to afford the desired bis(isoxazolidine) products with excellent stereocontrol. The resulting bis(isoxazolidine) products produced from two systems were reduced with Zn/MeOH to induce reductive N–O cleavages, yielding branched polyaminols stereoselectively.

Graphical abstract: Stereoselective annulation between an allene, an alkene, and two nitrosoarenes to access bis(isoxazoliodine) derivatives

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Publication details

The article was received on 21 Aug 2017, accepted on 25 Oct 2017 and first published on 25 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02087B
Citation: Org. Biomol. Chem., 2017,15, 9389-9397
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    Stereoselective annulation between an allene, an alkene, and two nitrosoarenes to access bis(isoxazoliodine) derivatives

    P. Sharma, P. D. Jadhav, M. Skaria and R. Liu, Org. Biomol. Chem., 2017, 15, 9389
    DOI: 10.1039/C7OB02087B

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