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Direct Organocatalytic Enantioselective Functionalization of SiO x Surfaces
Author(s) -
Parkin John D.,
Chisholm Ross,
Frost Aileen B.,
Bailey Richard G.,
Smith Andrew D.,
Hähner Georg
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201804814
Subject(s) - enantioselective synthesis , monolayer , surface modification , enantiomer , adsorption , catalysis , silicon , materials science , oxide , chemical engineering , nanotechnology , molecule , combinatorial chemistry , chemistry , organic chemistry , engineering
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.