New Chiral Hypervalent Iodine Compounds in Asymmetric Synthesis

The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent...

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Bibliographic Details
Published in:Journal of organic chemistry 1998-10, Vol.63 (22), p.7674-7679
Main Authors: Hirt, Urs H, Spingler, Bernhard, Wirth, Thomas
Format: Article
Language:English
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Summary:The synthesis of new chiral hypervalent iodine compounds 3 and their use in asymmetric oxidative functionalizations are described. The substituents in the chiral moiety and the stereoelectronic properties of the reagents 3, as well as the reaction conditions, have been optimized. Chiral hypervalent iodine compounds 3 have been investigated in the asymmetric dioxytosylation of styrene and in the α-oxytosylation of propiophenone as test reactions. X-ray structural analysis of some reagents shows an interaction between the chiral moiety and the iodine resulting in stereoselectivities up to 53% ee in the products.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo980475x