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Letter

Sulfonimidamides: Efficient Chiral Iminoiodane Precursors for Diastereoselective Copper-Catalyzed Aziridination of Olefins

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Pablo H. Di Chenna, Fabien Robert-Peillard, Philippe Dauban,* and Robert H. Dodd*;

Institut de Chimie des Substances Naturelles, CNRS, avenue de la terrasse, F-91198 Gif-sur-Yvette, France

Org. Lett., 2004, 6 (24), pp 4503–4505

DOI: 10.1021/ol048167a

Publication Date (Web): November 3, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, philippe.dauban@icsn.cnrs-gif.fr, ; , robert.dodd@icsn.cnrs-gif.fr

Abstract

N-(p-Toluenesulfonyl)-p-toluenesulfonimidamide reacts with iodosylbenzene to afford in situ a chiral iminoiodane. The latter gives, in the presence of a copper(I) catalyst, a nitrene that is very efficiently transferred under stoichiometric conditions to a variety of alkenes with diastereoselectivities up to 60%.

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Published In Issue November 25, 2004
Received September 10, 2004

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Letter

Sulfonimidamides: Efficient Chiral Iminoiodane Precursors for Diastereoselective Copper-Catalyzed Aziridination of Olefins

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Toward a Synthetically Useful Stereoselective C−H Amination of Hydrocarbons

Asymmetric Synthesis of Diamine Derivatives via Sequential Palladium and Rhodium Catalysis

Efficient Copper-Mediated Reactions of Nitrenes Derived from Sulfonimidamides

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