Synthesis of indoles via a tandem benzannulation-cyclization strategy
Name
370422528-MIT.pdf
Description
Full printable version
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9.58 MB
Format
Adobe PDF
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fe8ec7735de9b6fb37faa7957ce5e062
Author(s)
Lam, Tin Yiu
Advisor(s)
Rick L. Danheiser.
Date Issued
2008
Publisher
Massachusetts Institute of Technology
Abstract
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.
Description
Vita.
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2008.
Includes bibliographical references.
Subjects
Chemistry.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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copyright. They may be viewed from this source for any purpose, but
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