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Electroreductive Intramolecular Coupling of 1-Indolealkanones

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posted on 16.10.2008, 00:00 by Naoki Kise, Toshiyuki Mano, Toshihiko Sakurai
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.