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Conformationally restricted dynamic supramolecular catalysts for substrate-selective epoxidations.

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Author

Summary, in English

A second generation of a substrate-selective dynamic supramolecular catalytic system consisting of a catalyst part and a receptor part, connected by a hydrogen-bonding motif, has been realized based on rational design. The results from analyses of the equilibrium mixture of the species generated by the components of the first generation system led us to selectively lock the cisoid conformation of the catalyst part to increase the amount of the substrate-selective catalytic cavity in the equilibrium mixture. This was realized by strapping the catalyst part by organic synthesis. This strapping led to an increase in substrate selectivity in the pair-wise competitive epoxidations of pyridyl- vs. phenyl-appended styrenes and pyridyl- vs. phenyl-appended stilbenes of both Z- and E- configuration compared to the first generation system, reaching 3.4 : 1 as the highest substrate selectivity for Z-mono-pyridyl-stilbene (27a) vs. the corresponding all-carbon analogue (28a) and for E-dipyridyl-stilbene (26b) vs. the corresponding all-carbon analogue (28b), respectively.

Publishing year

2012

Language

English

Pages

2059-2067

Publication/Series

Organic and Biomolecular Chemistry

Volume

10

Issue

10

Document type

Journal article

Publisher

Royal Society of Chemistry

Topic

  • Organic Chemistry

Status

Published

ISBN/ISSN/Other

  • ISSN: 1477-0539