Transition Metal Catalysis for Heteroarene Dearomatization and Natural Product Synthesis (2022-09-09)
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Transition Metal Catalysis for Heteroarene Dearomatization and Natural Product Synthesis (2022-09-09)
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2022
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Abstract
Non-aromatic nitrogen containing heterocycles such as
dihydropyridines, tetrahydropyridines and piperidines are common
structural motifs in drug molecules and natural products. Due to their
widespread presence in bioactive molecules, synthesis of such
heterocycles has attracted significant attention of the synthetic
community. Despite the past efforts, methods for the catalytic
stereoselective synthesis of dihydropyridines and piperidines is
limited. We will discuss our studies toward the synthesis of
dihydropyridines and related partially saturated heteroarenes
through dearomatization of corresponding aromatic heteroarenes.
These reactions are catalyzed by variety of transition metal catalysts
and proceed in excellent yield, regioselectivity and
enantioselectivity, and tolerate a wide range of functional groups
such as ester, ketone, amide, halogen and primary alcohol.
Chemoselective reactions of the remaining double bonds of the
reaction products, dihydroheteroarenes, enables their conversion to
saturated nitrogen heterocycles. Factors that influence the reaction
yield, enantioselectivity, regioselectivity of the reactions as well as
applications of these transition metal catalyzed reactions to natural
product synthesis will also be discussed.
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Friday, September 9, 2022, 3:00 p.m.; Chem 200; Dr. Rashad Karimov, Assistant Professor, Department of Chemistry & Biochemistry, Auburn University; Host - Dr. Viktor Zhdankin
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Fall 2022 Seminar Series
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Karimov, Rashad; University of Minnesota Duluth. Department of Chemistry and Biochemistry. (2022). Transition Metal Catalysis for Heteroarene Dearomatization and Natural Product Synthesis (2022-09-09). Retrieved from the University Digital Conservancy, https://hdl.handle.net/11299/242047.
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