Dr. Kristyna Pluhackova

The discovery of proline as organocatalyst revolutionized organic chemistry by enabling enantioselective synthesis with small organic molecules. In our interdisciplinary work, we join organic chemistry, material science and molecular dynamics simulations in order to unveil the role of confinement of proline organocatalyst by enclosing it in a metal organic frameworks (MOF) of different size. In detail, the cubic Zr-based UiO frameworks consists of a metallic center and 12 linkers of tunable length, i.e. phenyl, biphenyl or terphenyl. Specific covalent attachment of the organocatalyst to these linkers opens the possibility to unravel the catalyst activity, diastereoselectivity and enantioselectivity in diverse confining surroundings. Moreover by varying the catalyst loadings of the framework we can fine tune the turnover of the reaction. Our results clearly show, that confining proline catalyst results in stereoselectivity flip of the products.