Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 1, Pages 129-134Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200700410
Keywords
basic alumina; carbanions; conjugate addition; heterogeneous catalysis; indoles
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Active methylene compounds and nitro derivatives react with 3-(1-arylsulfonylalkyl)-indoles in the presence of potassium fluoride on basic alumina at room temperature leading to the corresponding adducts in good yields. Under basic conditions, sulfonylindoles suffer elimination of arenesulfinic acid leading to an intermediate vinylogous imine that promptly adds stabilized carbanions. The obtained 3-indolyl derivatives are pivotal intermediates for the synthesis of indole-based alkaloids and amino acids.
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