Date of Completion


Document Type

Honors College Thesis



Thesis Type

College of Arts and Science Honors, Honors College

First Advisor

Matthias Brewer


Synthetic organic chemistry, conjugate additions, stereocontrol


Conjugate additions are powerful chemical reactions in organic synthesis that allow for the formation of new carbon-carbon bonds. The Brewer group developed a diazo-retentive conjugate addition that allows for the addition of carbon nucleophiles to vinyl diazoniums. This reaction produces highly congested carbon centers, while retaining the versatile diazo functional group. The retention of the diazo group allows for further transformations of the products to create complex small molecules. 1,3 – dipolar cycloadditions with the conjugate addition products and a dipolarophile were studied to give highly substituted bi- and tri-cyclic tetrahydrofurans. This work explores OH insertions of the reduced conjugate addition products to give highly substituted monocyclic tetrahydrofurans. Formation of dihydrofurans from the conjugate addition products was also explored; however, these were not obtained in synthetically useful yields.

Additionally, the conjugate addition is not enantioselective, meaning the 3D orientation of these products cannot be controlled. The 3D orientation of molecules affects biological activities, thus, it is imperative to control the orientation of molecules produced in a bond-forming reaction. This work looks at synthesizing and assessing chiral organocatalysts for the conjugate addition to render it enantioselective. Thiourea, squaramide, phosphoric acid, and silanediol catalysts were explored; however, none of these catalysts induced significant enantioselectivity.

This work then looks at achieving the diastereoselective conjugate addition via the incorporation of chiral auxiliaries. This was more successful, and using Oppolzer’s camphorsultam as the chiral auxiliary, a diastereoselective conjugate addition was achieved when the reaction was run at room temperature in methyl-tert­-butyl ether to give the product in a 33 : 1 diastereomeric ratio. Future work consists of cleaving the chiral auxiliary group and testing the enantioselectivity of this reaction.

Creative Commons License

Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

Available for download on Tuesday, November 11, 2025