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Synthesis of indoles via a tandem benzannulation-cyclization strategy

Author(s)
Lam, Tin Yiu
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Massachusetts Institute of Technology. Dept. of Chemistry.
Advisor
Rick L. Danheiser.
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M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission. http://dspace.mit.edu/handle/1721.1/7582
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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.
 
Date issued
2008
URI
http://hdl.handle.net/1721.1/46045
Department
Massachusetts Institute of Technology. Department of Chemistry
Publisher
Massachusetts Institute of Technology
Keywords
Chemistry.

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