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Issue 8, 2018
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Chiral auxiliary recycling in continuous flow: automated recovery and reuse of Oppolzer's sultam

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Abstract

The telescoping of a three-stage, chiral auxiliary-mediated transformation in flow is described, including continuous separation of the product and auxiliary. The auxiliary can either be collected for later reuse, or directly fed back to the beginning of the process for recycling in real time, enabling each molecule of auxiliary to make multiple equivalents of chiral product and thus minimizing the step- and atom-economy issues associated with auxiliary-mediated synthesis. This concept is demonstrated for the asymmetric hydrogenation of olefins using Oppolzer's sultam, shortening the total reaction time >100 fold compared to batch, and demonstrating formal sub-stoichiometric auxiliary loading with respect to the process by automating auxiliary recycling within a closed loop.

Graphical abstract: Chiral auxiliary recycling in continuous flow: automated recovery and reuse of Oppolzer's sultam

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Publication details

The article was received on 06 Dec 2017, accepted on 17 Jan 2018 and first published on 25 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC05192A
Citation: Chem. Sci., 2018,9, 2130-2134
  • Open access: Creative Commons BY license
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    Chiral auxiliary recycling in continuous flow: automated recovery and reuse of Oppolzer's sultam

    R. J. Sullivan and S. G. Newman, Chem. Sci., 2018, 9, 2130
    DOI: 10.1039/C7SC05192A

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