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2 article(s) from Ward, Thomas R

Aqueous olefin metathesis: recent developments and applications

Valerio Sabatino and
Thomas R. Ward

Beilstein J. Org. Chem. 2019, 15, 445–468, doi:10.3762/bjoc.15.39

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Graphical Abstract

Scheme 1: Most common metathesis reactions. Ring-opening metathesis polymerization (ROMP), acyclic diene meta...

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Scheme 2: Catalytic cycle for metathesis proposed by Chauvin.

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Figure 1: Some of the most representative catalysts for aqueous metathesis. a) Well-defined ruthenium catalys...

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Scheme 3: First aqueous ROMP reactions catalyzed by ruthenium(III) salts.

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Scheme 4: Degradation pathway of first generation Grubbs catalyst (G-I) in methanol.

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Scheme 5: Synthesis of Blechert-type catalysts 19 and 20.

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Figure 2: Chemical structure and components of amphiphilic molecule PTS and derivatives.

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Scheme 6: RCM of selected substrates in the presence of the surfactant PTS. Conditions^a: The reaction was car...

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Scheme 7: RCM reactions of substrates 31 and 33 with the encapsulated G-II catalyst.

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Scheme 8: Living ROMP of norbornene derivatives 35 and 36 with phosphine-based catalysts bearing quaternary a...

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Scheme 9: Synthesis of water-soluble catalysts 3 and 4 bearing quaternary ammonium tags.

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Scheme 10: In situ formation of catalyst 5 bearing a quaternary ammonium group.

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Scheme 11: Catalyst recycling of an ammonium-bearing catalyst.

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Scheme 12: Removal of the water-soluble catalyst 12 through host–guest interaction with silica-gel-supported β...

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Scheme 13: Selection of artificial metathases reported by Ward and co-workers (ArM 1 based on biotin–(strept)a...

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Figure 3: In vivo metathesis with an artificial metalloenzyme based on the biotin–streptavidin technology.

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Scheme 14: Artificial metathase based on covalent anchoring approach. α-Chymotrypsin interacts with catalyst 66...

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Scheme 15: Assembling an artificial metathase (ArM 4) based on the small heat shock protein from M. Jannaschii...

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Scheme 16: Artificial metathases based on cavity-size engineered β-barrel protein nitrobindin (NB4exp). The HG...

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Scheme 17: Artificial metathase based on cutinase (ArM 8) and resulting metathesis activities.

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Scheme 18: Site-specific modification of proteins via aqueous cross-metathesis. The protein structure is based...

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Scheme 19: a) Allyl homocysteine (Ahc)-modified proteins as CM substrates. b) Incorporation of Ahc in the Fc p...

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Scheme 20: On-DNA cross-metathesis reaction of allyl sulfide 99.

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Scheme 21: Preparation of BODIPY-containing profluorescent probes 102 and 104.

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Scheme 22: Metathesis-based ethylene detection in live cells.

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Scheme 23: First example of stapled peptides via olefin metathesis.

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Review

Published 14 Feb 2019

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Profluorescent substrates for the screening of olefin metathesis catalysts

Raphael Reuter and
Thomas R. Ward

Beilstein J. Org. Chem. 2015, 11, 1886–1892, doi:10.3762/bjoc.11.203

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Figure 1: Catalysts 1–4 tested for the metathesis of profluorescent substrates.

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Scheme 1: Two profluorescent substrates yielding fluorescent products upon ring-closing metathesis.

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Scheme 2: Synthesis of the two profluorescent substrates amenable to ring-closing metathesis.

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Figure 2: Fluorescence evolution resulting from closing metathesis of umbelliferone precursor 8 (λ_excitation ...

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Figure 3: Fluorescence evolution resulting from closing metathesis of fluorescence–quencher substrate 5 (λ_exc...

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Figure 4: Comparison of kinetics measured by HPLC a) and by a plate reader b) for the ring-closing metathesis...

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Full Research Paper

Published 12 Oct 2015

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