Direct Organocatalytic Enantioselective Functionalization of SiOx Surfaces. Issue 30 (29th June 2018)

• Record Type: Journal Article
• Authors: Parkin, John D.; Chisholm, Ross; Frost, Aileen B.; Bailey, Richard G.; Smith, Andrew D.; Hähner, Georg
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 30(2018)
• Page Start: 9377
• Page End: 9381
• Publication Date: 2018-06-29
• Subjects: chirality -- heterogeneous catalysis -- organocatalysis -- scanning probe microscopy -- surface chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201804814
• Languages: English
• ISSNs: 1433-7851

Abstract

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