2026-09-20T13:25:11Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/685442022-01-13T07:54:21Zcom_1721.1_7582com_1721.1_7581col_1721.1_131022
Rick L. Danheiser.
Fontaine, Shaun D. (Shaun David)
Massachusetts Institute of Technology. Dept. of Chemistry.
Massachusetts Institute of Technology. Department of Chemistry
2012-01-12T19:36:09Z
2012-01-12T19:36:09Z
2011
2011
http://hdl.handle.net/1721.1/68544
771921793
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2011.
Vita. Cataloged from PDF version of thesis.
Includes bibliographical references.
Iminoacetonitriles participate as reactive dienophiles in intramolecular Diels-Alder cycloadditions affording quinolizidines and indolizidines. The resulting a-amino nitrile cycloadducts are versatile intermediates that can be further elaborated in a stereoselective manner. This thesis describes the development of intramolecular, enantioselective aza Diels- Alder cycloadditions promoted by chiral Brønsted acids as well as the discovery that iminoacetonitriles can also participate in acid catalyzed cycloadditions. The second part of this thesis reports the total synthesis of (-)-quinolizidine 2071 using an intramolecular, enantioselective cycloaddition of an iminoacetonitrile as the key step.
by Shaun D. Fontaine.
Ph.D.
331 p.
eng
Massachusetts Institute of Technology
M.I.T. theses are protected by
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http://dspace.mit.edu/handle/1721.1/7582
Chemistry.
Enantioselective [4 + 2] cycloadditions of iminoacetonitriles : application to the total synthesis of (-)-quinolizidine 2071
Thesis
application/pdf
Publication
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<Abstract>Iminoacetonitriles participate as reactive dienophiles in intramolecular Diels-Alder cycloadditions affording quinolizidines and indolizidines. The resulting a-amino nitrile cycloadducts are versatile intermediates that can be further elaborated in a stereoselective manner. This thesis describes the development of intramolecular, enantioselective aza Diels- Alder cycloadditions promoted by chiral Brønsted acids as well as the discovery that iminoacetonitriles can also participate in acid catalyzed cycloadditions. The second part of this thesis reports the total synthesis of (-)-quinolizidine 2071 using an intramolecular, enantioselective cycloaddition of an iminoacetonitrile as the key step.</Abstract>
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