Electroreductive intramolecular coupling of 1-indolealkanones |
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| Authors: | Kise Naoki Mano Toshiyuki Sakurai Toshihiko |
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| Affiliation: | Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Koyama, Tottori 680-8552, Japan. kise@bio.tottori-u.ac.jp |
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| Abstract: | The electroreduction of 1-indolealkanones in isopropanol gave five-, six-, and seven-membered trans-cyclized products stereospecifically. On the other hand, the electroreduction of 3-methoxycarbonyl-1-indolealkanones afforded mixtures of two diastereomers of the corresponding trans- and cis-cyclized products. The DFT calculations for the radical anions support that the reductive couplings of 1-indolealkanones and 3-methoxycarbonyl-1-indolealkanones proceed through different reaction mechanisms. |
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