2026-09-20T11:52:16Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/397392022-01-13T07:54:21Zcom_1721.1_7582com_1721.1_7581col_1721.1_131022
Rick L. Danheiser.
Maloney, Kevin M. (Kevin Matthew)
Massachusetts Institute of Technology. Dept. of Chemistry.
Massachusetts Institute of Technology. Department of Chemistry
2007-12-07T16:16:35Z
2007-12-07T16:16:35Z
2007
2007
http://hdl.handle.net/1721.1/39739
181375762
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2007.
Vita.
Includes bibliographical references.
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'.
by Kevin M. Maloney.
Ph.D.
266 leaves
eng
Massachusetts Institute of Technology
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
Chemistry.
[4+2] cycloadditions of iminoacetonitriles : a general strategy for the synthesis of quinolizidines, indolizidines, and piperidines
Thesis
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<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'.</Abstract>
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