Stereoselective Radical Azidooxygenation of Alkenes

Bo Zhang and Armido Studer*

*Institute of Organic Chemistry, Westfälische Wilhems-University, Corrensstrasse 40, 48149, Münster, Germany, Email: studeruni-muenster.de

B. Zhang, A. Studer, Org. Lett., 2013, 15, 4548-4551.

DOI: 10.1021/ol402106x

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Abstract

A readily prepared N₃-iodine(III) reagent acts as a clean N₃-radical precursor in a radical azidooxygenation of various alkenes in the presence of TEMPONa as a mild organic reducing reagent. The C-radical generated after N₃-radical addition is efficiently trapped by in situ generated TEMPO. Yields are very good, and for cyclic systems azidooxygenation occurs with excellent diastereoselectivity.

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Key Words

1,2-azido alcohols, 1,2-amino alcohols

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ID: J54-Y2013