Imprinted polymers and nanogels have proven to be versatile entities that have been employed in a variety of applications due to their small size, stability, and excellent selectivity. They have been utilized in the resolution of racemic mixtures, in chromatographic purifications, and as artificial antibodies. In addition, imprinted polymers and nanogels have been shown to be effective enzyme mimics for transformations that include Diels-Alder reactions, asymmetric hydrogenations, and dehydrofluorination reactions. Appealing aspects of imprinted polymers employed as enzyme mimics include their ability to be recycled multiple times, that they possess a high level of stability to harsh reaction conditions, and that they can be synthesized to possess a single catalytic active site per nanogel particle. Herein, we report the initial development of a Baeyer-Villiger enzyme mimic. Specifically, we have investigated the synthesis of a competent transition state analog that will be used to imprint the active site of the nanogel; this is the most critical aspect of the project because the transition state analog is utilized to define the shape and size of the active site within the imprinted nanogel. At the onset of this project, cyclohexanol was converted to 2,2,6,6-tetrachlorocyclohexanone, which was then further transformed to 2,2,6,6-tetrafluorocyclohexanone. 2,2,6,6-tetrafluorocyclohexanone is currently being functionalized with peracrylic acid to afford the transition state analog that shall be utilized to imprint the nanogel. Further studies are in progress to access the most robust and efficient Baeyer-Villiger enzyme mimic.

Synthesis of transition state analogs for application in Baeyer-Villiger enzyme mimics

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.