Journal
TETRAHEDRON
Volume 56, Issue 5, Pages 791-804Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(99)01051-0
Keywords
indoles; nitrones; hydroxylamines; natural products
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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-indolylhydroxylamines were isolated. The diastereoselectivity of this condensation with a nitrone derived from cysteine was investigated. A method for the introduction of an alkylhydroxylamino group onto position 2 of indole, the synthesis of three natural 3,3'-diindolylalkanes and of non-symmetric diindolylalkanes are also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.
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