Abstract
Due to the importance of hydrazines and hydroxylamines as biologically active compounds, the development of stereoselective methods for their preparation constitutes an important task in asymmetric synthesis. However, a limited number of general synthetic protocols have been developed thus far. The authors report the efficient preparation of chiral hydrazines and hydroxylamines via palladium-catalyzed amination of vinyl epoxide in the presence of the Trost biphosphine ligand 1. Reactions generally proceed regioselectively, furnishing the corresponding branched products with high yields and enantio-selectivities up to 97% ee. Synthetic power of this protocol has been demonstrated via a concise synthesis of (R)-piperazic acid accomplished in five steps in 41% overall yield.
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