Journal
TETRAHEDRON
Volume 64, Issue 23, Pages 5435-5441Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.04.014
Keywords
conjugate addition; heterogeneous catalysis; indoles; nitroaldol reaction; nitroalkenes
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Ethyl 3-nitro-2-alkenoates can be generated starting from nitroalkanes and ethyl 2-oxoacetate under heterogeneous conditions that minimize work-up procedures, avoid any purification step and direct manipulation of the nitroalkene system. Reaction of ethyl 3-nitro-2-alkenoates, formed in situ from their acetoxy precursors, with indoles in the presence of basic alumina affords ethyl 2-(3-indolyl)-3-nitro-alkanoates that are central intermediates for the preparation of tryptamines and carboline alkaloids. A base promoted elimination of nitrous acid from these nitroindolyl derivatives readily produces ethyl 2-(3-indolyl)-2-alkenoates with high E stereoselectivity. The latter compounds can be used as Michael acceptors in intra- and intermolecular reactions with nucleophilic reagents. (C) 2008 Elsevier Ltd. All rights reserved.
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