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Issue 30, 2018
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Asymmetric iodine catalysis-mediated enantioselective oxidative transformations

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The implementation of chiral iodine catalysis has tremendously been developed in the field of asymmetric synthesis over the past decade. It enables the stereoselective creation of C–O as well as C–C, C–N and C–X (X = halogen) bonds through oxidative transformations. Thanks to the low toxicity and ease of handling of iodine compounds, this strategy offers many advantages over classical metal-catalyzed oxidations with chiral ligands. The approaches rely on iodine(I/III) or (−I/+I) catalysis by using a chiral aryliodine or ammonium iodide respectively in combination with a suitable terminal oxidant. As such, the design of iodine compounds with central, axial or even planar chirality has allowed us to achieve high enantioselectivities. The goal of this review is to cover the different chiral iodine compound-catalyzed oxidative transformations including α-functionalization of carbonyl compounds, dearomatization of phenol derivatives and difunctionalization of alkenes which should demonstrate that iodine catalysis has now found its place in the realm of asymmetric organocatalysis.

Graphical abstract: Asymmetric iodine catalysis-mediated enantioselective oxidative transformations

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Publication details

The article was received on 11 Jun 2018, accepted on 13 Jul 2018 and first published on 13 Jul 2018

Article type: Review Article
DOI: 10.1039/C8OB01378K
Citation: Org. Biomol. Chem., 2018,16, 5386-5402

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    Asymmetric iodine catalysis-mediated enantioselective oxidative transformations

    A. Claraz and G. Masson, Org. Biomol. Chem., 2018, 16, 5386
    DOI: 10.1039/C8OB01378K

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