Short Synthesis of Enantiopure trans-3-Arylpiperazine-2-carboxylic Acid Derivatives via Diaza-Cope Rearrangement

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• 作者：Soon Ho Kwon ; Sang Min Lee ; Sang Moon Byun ; Jik Chin ; B. Moon Kim
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：July 20, 2012
• 年：2012
• 卷：14
• 期：14
• 页码：3664-3667
• 全文大小：231K
• 年卷期：v.14,no.14(July 20, 2012)
• ISSN：1523-7052

文摘

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.