A highly diastereoselective [2,3]-sigmatropic N,O rearrangement

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Steven D. Bull, Stephen G. Davies, Simon Jones, Jacqueline V. A. Ouzman, Anne J. Price and David J. Watkin


Abstract

Lithium (E)-N-benzyl-O-(4-methoxy-4-phenylbut-2-enyl)- hydroxylamide undergoes a highly diastereoselective rearrangement via a chelated transition state, to afford after reduction, syn-3-benzylamino-4-methoxy-4-phenylbut-1-ene as a single diastereoisomer.


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