“Where chemistry meets creativity to shape the future”
Our research involves new synthetic method development and their application to the synthesis of structurally novel and biologically active natural products. Metal-catalyzed reactions to merge alkenes and alkynes to construct multiply unsaturated molecular structures are one of the major research interests. Aryne formation from tri- and tetraynes followed by exploiting their reactivity to develop novel transformation is another active area of our research. The reaction between lithiated trimethylsilyldiazomethane and unsaturated carbonyl compound followed by proteolytic cleavage of N–N bond constitutes a formal 1,2-aminocyanation, which is under investigation for the construction of amino quaternary carbon-containing molecules including amathspiramides and massadine.
DAESUNG LEE
RESEARCH
GROUP
University of Illinois Chicago
RESEARCH AREAS
Our research focuses on developing new synthetic methods and applying them to create novel, biologically active natural products. We explore metal-catalyzed reactions, particularly using ruthenium, to form complex carbon structures. Additionally, we investigate the unique reactivity of arynes and trimethylsilyldiazomethane to discover innovative transformations and applications in organic synthesis.
Aryne Chemistry
We explored the reactivity of arynes, generated via the hexadehydro Diels-Alder reaction, with various nucleophiles in both intra- and intermolecular reactions. Our studies include metal-catalyzed reactions like C–H insertion, hydroarylation, hydride transfer, and hydrohalogenation, as well as uncatalyzed reactions such as Alder-ene, 1,3-dipolar cycloadditions, and nucleophile additions. Notable applications include the synthesis of herbindole B and selaginpulvilins, demonstrating the effectiveness of aryne-based methods. Herbindole B synthesis involved aryne hydrohalogenation, while selaginpulvilins synthesis used aryne intermediates and various coupling reactions, highlighting the utility of aryne chemistry in constructing complex natural products.
TMSCHN2
Development
We explored the reactivity of arynes, generated via the hexadehydro Diels-Alder reaction, with various nucleophiles in both intra- and intermolecular reactions. Our studies include metal-catalyzed reactions like C–H insertion, hydroarylation, hydride transfer, and hydrohalogenation, as well as uncatalyzed reactions such as Alder-ene, 1,3-dipolar cycloadditions, and nucleophile additions. Notable applications include the synthesis of herbindole B and selaginpulvilins, demonstrating the effectiveness of aryne-based methods. Herbindole B synthesis involved aryne hydrohalogenation, while selaginpulvilins synthesis used aryne intermediates and various coupling reactions, highlighting the utility of aryne chemistry in constructing complex natural products.
Ruthenium
Catalyzed Reactions
Olefin metathesis, recognized by the 2005 Nobel Prize, is a key method for carbon-carbon formation. Ruthenium-alkylidene carbenes, or “Grubbs catalysts,” are stable and widely used in synthesizing natural products, pharmaceuticals, and polymers. This environmentally friendly method has seen less development in enyne metathesis, which involves both alkenes and alkynes. Our research advances enyne metathesis, revealing novel transformations like highly conjugated oligo-enynes and 1,4-hydrovinylative cyclization, aiding in the synthesis of natural products and amphidinolide V. We aim to develop new ruthenium complexes to discover novel reactivities and applications.
Meet the minds behind the innovation. Our team of dedicated researchers and scientists is passionate about advancing the frontiers of chemical synthesis. With diverse expertise in metal-catalyzed reactions and the exploration of novel intermediates, we collaborate to unlock new possibilities in organic chemistry.
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2024