Electroreductive intramolecular coupling of 1-indolealkanones.
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.
Kise
Naoki
N
Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Koyama, Tottori 680-8552, Japan. kise@bio.tottori-u.ac.jp
Mano
Toshiyuki
T
Sakurai
Toshihiko
T