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Issue 9, 2014
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Iron-catalyzed kinetic resolution of N-sulfonyl oxaziridines

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Abstract

We have developed a highly selective kinetic resolution of N-sulfonyl oxaziridines. This reaction utilizes an inexpensive and easily synthesized iron bis(oxazoline) catalyst to promote the efficient rearrangement of oxaziridines to the corresponding N-sulfonyl imides; no sacrificial reagents are required to effect this resolution. This process is readily translated to gram scale, which provides a practical method for the preparation of structurally diverse, enantiopure N-sulfonyl oxaziridines for use as reagents in organic synthesis.

Graphical abstract: Iron-catalyzed kinetic resolution of N-sulfonyl oxaziridines

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Publication details

The article was received on 10 May 2014, accepted on 13 Jun 2014 and first published on 16 Jun 2014


Article type: Edge Article
DOI: 10.1039/C4SC01371A
Chem. Sci., 2014,5, 3524-3527

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    Iron-catalyzed kinetic resolution of N-sulfonyl oxaziridines

    K. S. Williamson, J. W. Sawicki and T. P. Yoon, Chem. Sci., 2014, 5, 3524
    DOI: 10.1039/C4SC01371A

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