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Drastic Enhancement of Activity in Iodane-Based α-Tosyloxylation of Ketones: Iodine(III) Does the Hypervalent Twist

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posted on 03.02.2012, 00:00 by Audrey-Anne Guilbault, Claude Y. Legault
A drastic enhancement in catalytic activity was observed by the introduction of steric hindrance ortho to the iodine atom of catalysts used for the α-tosyloxylation of ketones. Through structural analysis and density functional theory calculations, we explain the origin of this acceleration effect and show its significance through a first example of a chiral catalyst exploiting this feature.