Direct Organocatalytic Enantioselective Functionalization of SiOx Surfaces

• DOI: 10.1002/anie.201804814
• Publication Date: 2018-06-05T16:35:45Z
• Authors: John D. Parkin; Ross Chisholm; Aileen B. Frost; Richard G. Bailey; Andrew D. Smith; Georg Hähner
• Keywords: Surface Modification

Traditional methods to prepare chiral surfaces involve either the adsorption of a molecule onto an achiral surface, or species that forms template creating lattices with long range order. To date only limited alternative strategies have been studied. In this manuscript "bottom-up" approach is developed allows preparation by direct enantioselective organocatalytic reactions on functionalized silicon oxide supported self-assembled monolayer (SAM). The efficient catalytic generation enantiomerically enriched organic achieved using commercially available homogeneous isothiourea catalyst promotes Michael-lactonization process upon silicon-oxide SAM reactive trifluoroenone group. Chiral atomic force microscopy (χ-AFM) used probe enantiomeric enrichment films measurement distributions arising from interaction d- l-cysteine-modified AFM tips and films.