N-sulfonyloxy carbamates as reoxidants for the tethered aminohydroxylation reaction.

Timothy J Donohoe, Majid J Chughtai, David J Klauber, David Griffin, Andrew D Campbell

Index: J. Am. Chem. Soc. 128 , 2514, (2006)

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Abstract

The use of N-sulfonyloxy carbamates as reoxidants for the tethered aminohydroxylation (TA) reaction is reported. These new conditions obviate the requirement for lithium hydroxide and tBuOCl in the oxidation mixture. In addition to providing aminohydroxylation products in good yields, the catalyst loadings can be reduced to just 1 mol % osmium. Moreover, for the first time, homoallylic alcohols are now viable substrates for the TA reaction.