Home
Resource
Development of amine alpha-functionalizations involving azomethine ylides intermediates
PDF
PDF format is widely accepted and good for printing.
Plug-in required
PDF-1(23.84 MB)
Citation & Export
View Usage Statistics
Staff View

Citation & Export
Hide

Simple citation

Richers, Matthew Tracy. Development of amine alpha-functionalizations involving azomethine ylides intermediates. Retrieved from https://doi.org/doi:10.7282/T3H133RB

Export

Click here for information about Citation Management Tools at Rutgers.

Statistics
Hide

Description

TitleDevelopment of amine alpha-functionalizations involving azomethine ylides intermediates
NameRichers, Matthew Tracy (author); Seidel, Daniel (chair); Knapp, Spencer (internal member); Williams, Lawrence J. (internal member); Wood, Harold B. (outside member); Rutgers University; Graduate School - New Brunswick
Date Created2015
Other Date2015-01 (degree)
SubjectChemistry and Chemical Biology, Ylides, Catalysts
Extent1 online resource (xii, 491 p. : ill.)
DescriptionThe α-functionalization of amines is a synthetic challenge of much interest to organic chemists. Common methods involve deprotonation with strong bases or oxidation with stoichiometric oxidants or transition metal catalysts. An alternative redox-neutral azomethine ylide-mediated approach to amine functionalization that harnesses the intrinsic reactivity of simple aldehyde and amine precursors without the need for harsh oxidants or bases will be detailed in this dissertation. The development of non-pericyclic amine annulations yielding aminal, N,O-acetal and N,S-thioacetal products will be discussed along with joint computational and experimental mechanistic studies on these reactions. The aminals are closely related to several naturally-occurring alkaloids and multiple methods were developed to synthesize these bioactive natural products and analogs. Additionally, two more azomethine ylide-based reactions will be discussed. The first is a variant on the classical Strecker reaction using α-amino acids which decarboxylatively gives rise to cyclic α-amino nitriles. Finally, a redox-neutral 1,5-electrocyclization reaction between secondary amines and α,β-unsaturated carbonyl compounds yielding amine heterocycles will be demonstrated.
NotePh.D.
NoteIncludes bibliographical references
Noteby Matthew Tracy Richers
Genretheses, ETD doctoral
Persistent URLhttps://doi.org/doi:10.7282/T3H133RB
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.
Version 8.5.5
Rutgers University Libraries - Copyright ©2024