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

29870577

DOI

10.1002/anie.201804814

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