Synthesis of indoles via a tandem benzannulation-cyclization strategy

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.

Department dc:contributor.department

Massachusetts Institute of Technology. Dept. of Chemistry.

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2008

Author dc:creator

• Lam, Tin Yiu

Advisor dc:contributor.advisor

• Rick L. Danheiser.

• Chemistry.

Statement dc:rights

• 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.

Licence dc:rights.uri

• http://dspace.mit.edu/handle/1721.1/7582

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/1721.1/46045

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/46045