Rh(III)-Catalyzed Alkene Difunctionalization for the Synthesis of Nitrogen-Containing Compounds
By: Sumin Lee
Publisher: [publisher not identified]
Published: 2021
Place of publication: [New York, N.Y.?]
Language: eng
Description: 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.
Notes: Department: Chemistry.

Thesis advisor: Tomislav Rovis.

Thesis (Ph.D.)--Columbia University, 2021.