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Flexible stereoselective functionalizations of ketones through umpolung with hypervalent iodine reagents

Mizar, Pushpak and Wirth, Thomas 2014. Flexible stereoselective functionalizations of ketones through umpolung with hypervalent iodine reagents. Angewandte Chemie International Edition 53 (23) , pp. 5993-5997. 10.1002/anie.201400405

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Abstract

The functionalization of carbonyl compounds in the α-position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or “umpolung”, we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel retrosynthetic planning and rapid assembly of structures previously accessible only by multistep sequences.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: amination; hydroxylation; hypervalent iodine; stereoselective synthesis; umpolung
Publisher: Wiley
ISSN: 1433-7851
Funders: EU Grant Number: 298642, School of Chemistry, Cardiff University
Last Modified: 07 Feb 2020 15:45
URI: http://orca-mwe.cf.ac.uk/id/eprint/60259

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