Enantioselective [4 + 2] cycloadditions of iminoacetonitriles : application to the total synthesis of (-)-quinolizidine 2071
Author(s)Fontaine, Shaun D. (Shaun David)
Massachusetts Institute of Technology. Dept. of Chemistry.
Rick L. Danheiser.
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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.
Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2011.Vita. Cataloged from PDF version of thesis.Includes bibliographical references.
DepartmentMassachusetts Institute of Technology. Dept. of Chemistry.
Massachusetts Institute of Technology