Stereoselective Synthesis of Diazaheterocycles by Decarboxylative Asymmetric Allylic Alkylation

Citation

Sun, Alexander Wang (2019) Stereoselective Synthesis of Diazaheterocycles by Decarboxylative Asymmetric Allylic Alkylation. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/E2YS-GJ06. https://resolver.caltech.edu/CaltechTHESIS:05132019-140157302

Abstract

The Stoltz group has developed transition-metal catalyzed methods to synthesize quaternary and tetrasubstituted stereocenters over the past fourteen years. Using iridium, palladium, copper, and nickel, the group has synthesized a myriad cyclic and acylic quaternary motifs of incredible synthetic and medicinal utility. This thesis presents several projects that further expand the scope of Pd-catalyzed decarboxylative allylic alkylation and examine its applications to the synthesis of medicinally important small molecules. The synthesis of chiral gem-disubstituted five-, six-, and seven-membered diazaheterocycles is presented. Their utility as building blocks for complex medicinal compounds is highlighted. Then, we explore the utility of gem-disubstituted heterocycles in the context of medicinal chemistry.

Thesis Files