Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

Beilstein Journal of Organic Chemistry

Shigeru Nishiyama¹  Taiki Kojima¹  Yasuaki Einaga¹  Tsuyoshi Saito²  Rika Obata³ 

[1] Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1 Kohoku-ku, Yokohama 223-8522, Japan;International Institute for Integrative Sleep Medicine, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan;Research and Education Center for Natural Sciences, Keio University, Hiyoshi 4-1-1 Kohoku-ku, Yokohama 223-8521, Japan;

关键词: boron-doped diamond (BDD) electrode;    cathodic reduction;    electrochemistry;    electrosynthesis;    neolignan;   

DOI  :  10.3762/bjoc.11.21

来源: DOAJ

【 摘 要 】

The electroreduction reaction of methyl cinnamate on a boron-doped diamond (BDD) electrode was investigated. The hydrodimer, dimethyl 3,4-diphenylhexanedioate (racemate/meso = 74:26), was obtained in 85% yield as the major product, along with small amounts of cyclic methyl 5-oxo-2,3-diphenylcyclopentane-1-carboxylate. Two new neolignan-type products were synthesized from the hydrodimer.

【 授权许可】

Unknown