Direct Organocatalytic Enantioselective Functionalization of SiOxSurfaces
Publication Date
2018
Journal Title
Angew Chem Int Ed Engl
Abstract
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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.
Volume Number
57
Issue Number
30
Pages
9377 - 9381
Document Type
Article
Status
Faculty
Facility
School of Medicine
Primary Department
Urology
PMID
DOI
10.1002/anie.201804814
