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Theses Doctoral

Rh(III)-Catalyzed Alkene Difunctionalization for the Synthesis of Nitrogen-Containing Compounds

Lee, Sumin

Nitrogen-containing compounds are essential structural units in a myriad of biologically active molecules including pharmaceuticals. Although numerous synthetic methods have been developed over the last few decades, new methods constructing them in an efficient way from readily accessible starting material are still great of interest. As a coupling partner of the reaction, alkenes are abundant, general, and therefore ideal starting materials to synthesize a variety of complex, value-added products. In this thesis, we have utilized Rh(III) catalysis to develop efficient synthetic methodologies for nitrogen-containing compounds using alkenes as coupling partners.

In Chapter 2, we developed a unique disconnection approach to pyrrolidines using a-olefins as a 4-carbon source and hydroxylamine derivatives as a nitrogen source of the reaction. In Chapter 3, regio- and diastereoselective synthesis of a,b-unsaturated-d-lactams from acrylamide and unactivated alkenes initiated from C-H activation are discussed. In Chapters 4 and 5, three-component alkene difunctionalization of alkenes delivering acyclic aminated products including a-amino acids are described.

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More About This Work

Academic Units
Chemistry
Thesis Advisors
Rovis, Tomislav
Degree
Ph.D., Columbia University
Published Here
June 16, 2021