Date of Award
Bachelor of Science
Dr. Emma Goldman
Dr. Raymond Dominey
Beta-chloroenals are readily accessible substances and are efficient precursors for a variety of heterocyclic compounds. Suzuki type cross-coupling reactions of such compounds with arylboronic acids yield 𝛃,𝛃-diarylacroleins with control of stereochemistry. The oxidation of these enals to the corresponding acids and subsequent oxidative lactonization leads to formation of the respective coumarins. The chemistry involved in these transformations with special attention to stereochemistry of the Suzuki coupling reaction will be discussed. A full NMR analysis involving 1H, 13C, COSY, NOESY, HSQC, and HMBC was performed to unambiguously confirm the structure and show that the reaction proceeds with retention of stereochemistry.
Carrick, William, "Stereochemical Control in Suzuki Cross Coupling Reactions of Acyclic (Z)-beta-haloacroleins" (2021). Honors Theses. 1591.