Piperazine-2-carboxylic acid can be regarded as an artificial amino acid and therefore has been utilized in many peptidomimetic structures for therapeutically important and biologically active compounds. Herein, an efficient synthetic method was developed for the construction of enantiomerically pure trans-3-arylpiperazine-2-carboxylic acid derivatives using diaza-Cope rearrangement (DCR) as a key step starting from (R,R)-1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane (hpen). A complete transfer of stereochemical integrity was observed for the transformation. Piperazine ring formation from the chiral  1,2-ethylenediamine derivatives using diphenylvinylsulfonium triflate followed by oxidation using  ruthenium(III) chloride monohydrate in the presence of sodium periodate provided the desired enantiopure trans-3-arylpiperazine-2-carboxylic acid derivatives.

Short route of optically pure <i>trans</i>-3-arylpiperazine-2-carboxylic acid derivatives

246th National Meeting (2013)

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Short route of optically pure trans-3-arylpiperazine-2-carboxylic acid derivatives