Synthesis of indoles via a tandem benzannulation-cyclization strategy
Author(s)Lam, Tin Yiu
Massachusetts Institute of Technology. Dept. of Chemistry.
Rick L. Danheiser.
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Vinylketenes (generated in situ from cyclobutenones or a-diazo ketones) react with ynamides via a pericyclic cascade process to produce highly-substituted aniline derivatives. Cyclization of the benzannulation products can then be achieved via several alternate procedures leading to indoles that are highly substituted on the six-membered ring. The cyclization approaches investigated as the second step in this tandem strategy included aromatic substitution, palladium-catalyzed oxidative amination, and nucleophilic cyclization. This thesis discusses the scope and limitations of this tandem strategy.
Vita.Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.Includes bibliographical references.
DepartmentMassachusetts Institute of Technology. Dept. of Chemistry.
Massachusetts Institute of Technology