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[4+2] cycloadditions of iminoacetonitriles : a general strategy for the synthesis of quinolizidines, indolizidines, and piperidines

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dc.contributor.advisor Rick L. Danheiser. en_US
dc.contributor.author Maloney, Kevin M. (Kevin Matthew) en_US
dc.contributor.other Massachusetts Institute of Technology. Dept. of Chemistry. en_US
dc.date.accessioned 2007-12-07T16:16:35Z
dc.date.available 2007-12-07T16:16:35Z
dc.date.copyright 2007 en_US
dc.date.issued 2007 en_US
dc.identifier.uri http://hdl.handle.net/1721.1/39739
dc.description Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2007. en_US
dc.description Vita. en_US
dc.description Includes bibliographical references. en_US
dc.description.abstract Iminoacetonitriles participate as reactive dienophiles in intermolecular and intramolecular Diels-Alder cycloadditions leading to quinolizidines, indolizidines, and piperidines. The resultant a-amino nitrile cycloadducts are versatile synthetic intermediates which can be further elaborated by stereoselective alkylation, reduction, reductive cyclization, and Bruylants reactions. The first part of this thesis describes the full details of our studies on the synthesis of iminoacetonitriles, the scope of their Diels-Alder reactions, and the synthetic elaboration of the a-amino nitrile cycloadducts to provide access to a variety of substituted quinolizidine and indolizidine derivatives. The second part of this thesis reports on the total synthesis of quinolizidine (-)-217A and our efforts directed toward the total synthesis of indolizidine (-)-235B'. en_US
dc.description.statementofresponsibility by Kevin M. Maloney. en_US
dc.format.extent 266 leaves en_US
dc.language.iso eng en_US
dc.publisher Massachusetts Institute of Technology en_US
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. en_US
dc.rights.uri http://dspace.mit.edu/handle/1721.1/7582
dc.subject Chemistry. en_US
dc.title [4+2] cycloadditions of iminoacetonitriles : a general strategy for the synthesis of quinolizidines, indolizidines, and piperidines en_US
dc.type Thesis en_US
dc.description.degree Ph.D. en_US
dc.contributor.department Massachusetts Institute of Technology. Dept. of Chemistry. en_US
dc.identifier.oclc 181375762 en_US


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