The adhesion of some marine organisms to almost any kind of surface in wet conditions has aroused increasing interest in recent decades. Numerous fundamental studies have been performed to understand the scientific basis of this behaviour, with catechols having been found to play a key role. Several novel bio-inspired adhesives and coatings with value-added performances have been developed by taking advantage of the knowledge gained from these studies. To date there has been no detailed overview focusing exclusively on the complex mode of action of these materials. The aim of this Review is to present recent investigations that elucidate the origin of the strong and versatile adsorption capacities of the catechol moiety and the effects of extrinsic factors that play important roles in the overall adhesion process, such as pH value, solvent, and the presence of metal ions. The aim is to detail the chemistry behind the astonishing properties of natural and synthetic catechol-based adhesive materials.

3 Stereochemistry AbstractTo create your abstract, type over the instructions in the template box below. Fonts or abstract dimensions should not be changed or altered. You may insert more abstracts by copying this box or by using the menu option to insert a stereochemistry abstract.J. Mancebo-Aracil , M. Martín-Rodríguez, C. Nájera, J. M. Sansano* , P. R. R. Costa, E. Crizanto de Lima, A. G Methyl (1S,3R,3aS,6aR)-5-methyl-3-phenyl-4,6-dioxooctahydro pyrrolo[3,4-c] Isopropyl (1S,3R,3aS,6aR)-5-methyl-3-phenyl-4,6-dioxoocta hydropyrrolo[3,4-c] Ethyl (1S,3R,3aS,6aR)-5-methyl-3-phenyl-4,6-dioxooctahydro pyrrolo[3,4-c] Methyl (1S,3R,3aS,6aR)-5-methyl-3-(2-naphthyl)-4,6-dioxoocta hydropyrrolo[3,4-c] tert- Butyl (1S,3R,3aS, Methyl (1S,3R,3aS,6aR)-5-methyl-4,6-dioxo-3-o-tolyloctahydropyrrolo[3,4-c] Methyl (1S,3R,3aS,6aR)-3-(2-chlorophenyl)-5-methyl-4,6-dioxooctahydropyrrolo[3,4-c] Methyl (1S,3R,3aS,6aR)-3-(3-pyridyl)-5-methyl-4,6-dioxooctahydropyrrolo[3,4-c] Methyl (1S,3R,3aS,6aR)-5-methyl-3-(4-methylphenyl)-4,6-dioxooctahydropyrrolo[3,4-c] Methyl (1S,3R,3aS,octahydropyrrolo [3,4-c] Methyl (1S,3R,3aS,6aR)-5-ethyl-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c] Methyl (1S,3R,3aS,6aR)-4,6-dioxo-3,5-diphenyloctahydropyrrolo[3,4-c] Methyl (1S,3R,3aS,6aR)-1,5-dimethyl-4,6-dioxo-3-phenyloctahydro pyrrolo[3,4-c] Methyl (1S,3R,3aS,6aR)-5-benzyl-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c] (1S,3R,3aS,6aR)-1 -isobutyl-5-methyl-4,6-dioxo-3-(2-thienyl)octahydropyrrolo [3,4-c] Methyl (1S,3R,3aS,6aR)-1-benzyl-5-methyl-4,6-dioxo-3-phenyl octahydropyrrolo[3,4-c] -indol-2-yl}-3,4-bis(phenylsulfonyl) Methyl (2R,3S,4S,5S)-5-[2-(2-acetoxyethyl)-4,5-dimethoxyphenyl]-3,4-bis(phenylsulfonyl) --- * Corresponding author. Tel.: +34-965903549; fax: +34-965903549; jmsansano@ua.es Methyl (1S,3R,3aS,6aR)-3-(4-chlorophenyl)-5-methyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate Methyl (2R,3R,4R,5S)-5-(naphth-2-yl)-3,4-bis(phenylsulfonyl) pyrrolidine-2-carboxylate Methyl (2R,3R,4R,5S)-5-phenyl-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate Methyl (2R,3R,4R,5S)-3,4-bis(phenylsulfonyl)-5-(o-tolyl)pyrrolidine-2-carboxylate Methyl (2R,3R,4R,5S)-5-(4-methoxyphenyl)-3,4-bis(phenylsulfonyl)pyrrolidine-2-carboxylate Methyl (2R,3R,4R,5S)-3,4-bis(phenylsulfonyl)-5-(p-tolyl)pyrrolidine-2-carboxylate Isopropyl (2R,3R,4R,5S)-5-(4-chlorophenyl)-3,4-bis(phenylsulfonyl) pyrrolidine-2-carboxylate Methyl (2R,3R,4R,5S)-3,4-bis(phenylsulfonyl)-5-(pyrid-3-yl) pyrrolidine-2-carboxylate Methyl (2R,3R,4R,5S)-5-{3-[2-((tert-butyldimethylsilyl)oxy)ethyl]-1-(phenylsulfonyl)-1H A R T I C L E I N F O AB S T R AC TArticle history: Received Received in revised form Accepted Available onlineBinap-AgSbF6 catalyzed 1,3-dipolar cycloaddition between azomethine ylides and electrophilic alkenes is described an compared with the analogous transformations mediated by other Binapsilver(I) salt complexes. Maleimides and 1,2-bis(phenylsulfonyl)ethylene, are suitable dipolarophiles to obtain very good enantioselections, even better enantioselections are generated by the multicompone...

The combination of the surface-adhesive properties of catechol rings and functional moieties conveyings pecific properties is very appealing to materials chemistry,b ut the preparation of catechol derivatives often requires elaborate synthetic routes to circumventt he intrinsic reactivity of the catechol ring. In this work, functional catechols are synthesized straightforwardly by using the bioinspired reaction of several functionalt hiols with o-benzoquinone. With one exception,t he conjugated addition of the thiol takes place regioselectively at the 3-positiono ft he quinone, and is rationalized by DFT calculations. Overall, this synthetic methodology provides ag eneral and straightforward access to functional andc hain-extended catechold erivatives, which are later tested with regard to their hydro-/oleophobicity, colloidal stability, fluorescence, and metal-coordinatingc apabilities in proof-of-concept applications.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.