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Palladium-Medicated Decarboxylative Cross-Coupling Reactions: Synthesis of Complex Polycyclic Amines

Ballard, Wendy Fields
Format
Thesis/Dissertation; Online
Author
Ballard, Wendy Fields
Advisor
McGarvey, Glenn
Chruma, Jason
Hoffman, Paul
Pu, Lin
Marshall, James
Abstract
Palladium-Mediated Decarboxylative Cross-Coupling Reactions: Synthesis of Complex Polycyclic Amines Wendy F. Ballard A variety of allyl and benzyl diphenylglycinate imine precursors were synthesized and they successfully underwent a facile palladium-catalyzed decarboxylative alkylation. 1-Iminoindanes 3 were synthesized from allyl diphenylglycinate imines 1 employing a microwave-promoted one-pot palladiumcatalyzed decarboxylative allylationHeck cyclization cascade. Variation of both the aryl and imine moieties furnished a diverse range of complex polycyclic imines amenable to the synthesis of biologically active natural products. General reaction conditions were also elucidated for the palladium-catalyzed decarboxylative benzylation of benzyl diphenylglycinate imines 4. Microwave irradiation greatly accelerated the transformation and various heteroaromatic moieties were tolerated in both the imine and ester components. Furthermore, this method has proved to be applicable toward the synthesis of a complex 2-aryl--carboline derivative. Note: Abstract extracted from PDF text
Language
English
Published
University of Virginia, Department of Chemistry, PHD, 2011
Published Date
2011-05-01
Degree
PHD
Collection
Libra ETD Repository
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