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New approaches to the synthesis of heterocyclic molecules
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Jarvis, Claire Lucy. New approaches to the synthesis of heterocyclic molecules. Retrieved from https://doi.org/doi:10.7282/T3N87DZX

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TitleNew approaches to the synthesis of heterocyclic molecules
NameJarvis, Claire Lucy (author); Seidel, Daniel (chair); Knapp, Spencer (internal member); Lee, Jeehiun Katherine (internal member); Wood, Harold Blair (outside member); Rutgers University; School of Graduate Studies
Date Created2018
Other Date2018-01 (degree)
SubjectChemistry and Chemical Biology, Heterocyclic compounds, Chemistry, Organic
Extent1 online resource (viii, 299 p. : ill.)
DescriptionWhether found in nature or made in the lab, small fused-ring heterocyclic molecules have found many medicinal applications. Making these molecules by building up structural complexity in a cheap and efficient manner is a driving force in organic synthesis, particularly when trying to gain access to a single enantiomer of the product. A number of synthetic approaches make use of stoichiometric and costly reagents, and involve multiple changes in the oxidation state of the product. Many of the enantioselective approaches rely on inefficient chiral auxiliaries or recrystallization techniques. This dissertation presents a new enantioselective approach to the synthesis of important lactam products, one that makes use of anion-binding by a thiourea organocatalyst to stabilize the ion pair intermediates. Enantioenriched gamma- and delta-lactams have been prepared by this approach. A method by which to synthesize useful N,S-acetals directly by combining their thiol and amine precursors, and which requires just a catalytic amount of organic acid, is also disclosed. The reaction mechanisms of these novel transformations are also explored.
NotePh.D.
NoteIncludes bibliographical references
Noteby Claire Lucy Jarvis
Genretheses, ETD doctoral
Persistent URLhttps://doi.org/doi:10.7282/T3N87DZX
Languageeng
CollectionSchool of Graduate Studies Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.
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