電子補助基を利用した窒素のα位炭素上への有機基の連続的導入法
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概要
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A method for sequential introduction of two organic groups on the same or the different α-carbons of nitrogen has been developed based on a combination of the concept of electroauxiliary and the cation pool method. Selective introduction of two carbon nucleophiles into 2,5- or 2,2-position of pyrrolidine has been accomplished via sequential electrochemical oxidation of pyrrolidine derivatives containing two silyl groups as the electroauxiliaries. Introduction of two carbon nucleophiles into 2,6-position of piperidine was also successful. The products having two olefinic groups were effectively converted to nitrogen-containing spiro compounds using ring closing metathesis, and an application to formal synthesis of cephalotaxine was also carried out. These results clearly illustrate the synthetic utility and potential of the present approach, and open a new aspect of the synthesis of nitrogen-containing compounds.
- 公益社団法人 電気化学会の論文
著者
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菅 誠治
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto Un
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Yoshida Jun-ichi
Department Of Biological Science Faculty Of Science Kumamoto University
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宋 春紅
Department Of Synthetic Chemistry And Biological Chemistry Graduate School Of Engineering Kyoto University
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渡辺 充
Department Of Synthetic Chemistry And Biological Chemistry Graduate School Of Engineering Kyoto University
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WATANABE Mitsuru
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University
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