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Palladium-Medicated Decarboxylative Cross-Coupling Reactions: Synthesis of Complex Polycyclic Amines634 views
Author
Ballard, Wendy Fields, Department of Chemistry, University of Virginia
Advisors
Marshall, James, Department of Chemistry, University of Virginia
Hoffman, Paul, Department of Medicine, University of Virginia
McGarvey, Glenn, Department of Chemistry, University of Virginia
Pu, Lin, Department of Chemistry, University of Virginia
Chruma, Jason, Department of Chemistry, University of Virginia
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 allylationHeck 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
Degree
PHD (Doctor of Philosophy)
Language
English
Rights
All rights reserved (no additional license for public reuse)
Ballard, Wendy Fields. Palladium-Medicated Decarboxylative Cross-Coupling Reactions: Synthesis of Complex Polycyclic Amines. University of Virginia, Department of Chemistry, PHD (Doctor of Philosophy), 2011-05-01, https://doi.org/10.18130/V3R85S.
