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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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Article information


Submitted
10 May 2014
Accepted
13 Jun 2014
First published
16 Jun 2014

Chem. Sci., 2014,5, 3524-3527
Article type
Edge Article

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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