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TitleDevelopment of redox-neutral reaction cascades
NameZhang, Chen (author), Seidel, Daniel (chair), Williams, Lawrence J (internal member), Zhang, Xumu (internal member), Ellsworth, Bruce (outside member), Rutgers University, Graduate School - New Brunswick,
Degree Date2010-10
Date Created2010
SubjectChemistry and Chemical Biology,
Oxidation-reduction reaction,
Cascades (Fluid dynamics)
DescriptionIn Chapter I, I give a general introduction to redox–neutral reaction cascades. In Chapter
II, a Lewis acid catalyzed formation of tetrahydroquinolines via an intramolecular rodox
process is described. Gadolinium triflate was proven to be a superior catalyst for this
transformation. More importantly, a catalytic enantioselective intramolecular redox
reaction was successfully achieved by the use of magnesium triflate in combination of a
DBFox ligand. In Chapter III, a novel transformation between o-aminobenzaldehyde and secondary cyclic amines is described. This novel transformation leads to synthetically useful cyclic aminal skeletons. Two natural products, deoxyvasicinone and rutaecarpine, were synthesized directly from the oxidation of the aminal skeletons. In addition, a onepot procedure for the synthesis of cyclic aminals promoted by Brønsted acids is also described, starting from o-aminobenzaldehydes and primary amines. In Chapter IV, nonconventional
functionalizations of azomethine ylides are described. Azomethine ylides are proven to be protonated by suitable proton sources, which results in the corresponding iminium ions. Nucleophiles can attack these iminium ions, leading to synthetically useful
skeletons.
II, a Lewis acid catalyzed formation of tetrahydroquinolines via an intramolecular rodox
process is described. Gadolinium triflate was proven to be a superior catalyst for this
transformation. More importantly, a catalytic enantioselective intramolecular redox
reaction was successfully achieved by the use of magnesium triflate in combination of a
DBFox ligand. In Chapter III, a novel transformation between o-aminobenzaldehyde and secondary cyclic amines is described. This novel transformation leads to synthetically useful cyclic aminal skeletons. Two natural products, deoxyvasicinone and rutaecarpine, were synthesized directly from the oxidation of the aminal skeletons. In addition, a onepot procedure for the synthesis of cyclic aminals promoted by Brønsted acids is also described, starting from o-aminobenzaldehydes and primary amines. In Chapter IV, nonconventional
functionalizations of azomethine ylides are described. Azomethine ylides are proven to be protonated by suitable proton sources, which results in the corresponding iminium ions. Nucleophiles can attack these iminium ions, leading to synthetically useful
skeletons.
NotePh.D.
NoteIncludes bibliographical references
NoteIncludes vita
Noteby Chen Zhang
Genretheses
Persistent URLhttp://hdl.rutgers.edu/1782.1/rucore10001600001.ETD.000056873
Languageeng
CollectionGraduate School - New Brunswick Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.