Direct organocatalytic enantioselective functionalization of SiOx surfaces
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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 of d- or l-cysteine-modified AFM tips and the organic films.
Parkin , J D , Chisholm , R , Frost , A B , Bailey , R G , Smith , A D & Hähner , G 2018 , ' Direct organocatalytic enantioselective functionalization of SiO x surfaces ' , Angewandte Chemie International Edition , vol. 57 , no. 30 , pp. 9377-9381 . https://doi.org/10.1002/anie.201804814
Angewandte Chemie International Edition
© 2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/anie.201804814
DescriptionWe thank the Engineering and Physical Sciences Research Council (GH, ADS and JDP acknowledge EP/K000411/1 and EP/L017008/1, and ADS and ABF acknowledge EP/J018139/1) and the Leverhulme Trust (GH and RGB acknowledge RPG2015-109). This work was supported by the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC grant agreement no. 279850. ADS thanks the Royal Society for a Wolfson Research Merit Award.
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