The reactions of nitrones with indoles

The reaction of nitrones with various indole derivatives has been studied. When the reaction was promoted by ClSiMe3, the isolated products were 3,3'- diindolylalkanes. With HCl as the activating reagent, 3-indolylhydroxylamin es were isolated. The diastereoselectivity of this condensation with a nitr one derived from cysteine was investigated. A method for the introduction o f an alkylhydroxylamino group onto position 2 of indole, the synthesis of t hree natural 3,3'-diindolylalkanes and of non-symmetric diindolylalkanes ar e also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.