title: Short synthesis of enantiopure trans-3-arylpiperazine-2-carboxylic acid derivatives via diaza-Cope rearrangement.
abstract: 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)/(S,S)-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.
authors: Department of Chemistry, College of Natural Sciences, Seoul National University , Seoul 151-747, South Korea, and Department of Chemistry, University of Toronto , Toronto, Ontario M5S 3H6, Canada.
authors: Soon Ho
authors: SH
authors: Kwon
authors: Sang Min
authors: SM
authors: Lee
authors: Sang Moon
authors: SM
authors: Byun
authors: Jik
authors: J
authors: Chin
authors: B Moon
authors: BM
authors: Kim
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005029:Ethylenediamines / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry*
chemical_list: C534973:1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane; D002264:Carboxylic Acids; D005029:Ethylenediamines; D010879:Piperazines; D013267:Stilbenes