Rhodium(III)-catalyzed oxidative couplings between N-sulfonyl allylamines and activated olefins have been achieved. Only olefination occurred for acrylates, and the butadiene product can be further cyclized under palladium-catalyzed aerobic conditions. The coupling with N,N-dimethylacrylamide followed a cyclization pathway.

The first chiral phosphine-catalyzed activation of acrylates for intramolecular formal [2 + 4] reactions with unsaturated imines is described. The catalytic reactions afford N-heterocycles with exceptionally high diastereo- and enantioselectivities. The [2 + 4] products are amenable for further transformations to useful molecules such as chiral piperidines and multicyclic structures.

A synthetic approach to highly functionalized cyclopentanes that incorporate adjacent secondary and tertiary alcohols is described. These systems, prepared in one step by a ketyl radical cyclization of β-disubstituted acrylates, represent the core of the marine prostanoid family of natural products.

Omniphobic fluorogel elastomers were prepared by photocuring perfluorinated acrylates and a perfluoropolyether crosslinker. By tuning either the chemical composition or the temperature that control the crystallinity of the resulting polymer chains, a broad range of optical and mechanical properties of the fluorogel can be achieved. After infusing with fluorinated lubricants, the fluorogels show...

Hydrogenation of a series of cyclic beta-(acylamino)acrylates with tetrasubstituted olefins has been accomplished successfully with the use of Ru catalysts with chiral biaryl ligands such as C3-TunaPhos, and up to over 99% ee's have been achieved. This methodology provides an efficient catalytic method for the synthesis of both cis and trans chiral cyclic beta-amino acid derivatives.

Cinnamic acid derivatives bearing a nitroxyl moiety (2,2,6,6-tetramethyl-1-oxyl-4-piperidyl 3-E-aryl acrylates) were synthesized in 30-100% yield using a Mizoroki-Heck cross-coupling reaction between 4-acryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl and iodobenzene derivatives in the presence of palladium(II) acetate coordinated with a tri(o-tolyl)phosphine ligand immobilized in a polyurea mat...

Beauticians are recognized as being at risk regarding the development of occupational skin diseases, mainly allergic contact dermatitis, with acrylates and methyisothiazolinones being the most frequently found occupational allergens (1–4). Little is known about behaviour at work regarding safety and the prevalence of skin symptoms in beautician apprentices. This article describes skin protectiv...

Reactions of(4S,5R)-1-(3,4-Dimethyl-2-oxo-5-phenylimidazolidine)carbonyl-isocyanate (4) with appropriate Baylis-Hillman adducts 5 gave the corresponding acyl carbamates 6,7 as equimolar diastereomeric mixtures. These mixtures were treated with DABCO, to afford with moderate diastereoselection easily separable [2-(3",4"-dimethyl-2"-oxo-5"-phenylimidazolidine-1-carboxamido)(aryl)methyl]acrylates ...

A rapid and divergent access to chiral azacyclic nucleoside analogues has been established via highly exo-selective and enantioselective 1,3-dipolar cycloaddition of azomethine ylides with β-nucleobase substituted acrylates. Using 1 mol% of a chiral copper complex, various chiral azacyclic nucleoside analogues were obtained in high yields, excellent exo-selectivities and enantioselectivities (9...

Using facile, highly modular synthetic approaches, a new monomer family based on a 1,2,3-triazole-4-vinyl building block has been prepared, and various functional derivatives have been obtained. Subsequent homo- and copolymerization of these novel functionalized monomers gives polymeric materials with unique physical properties, combining many attractive features of more traditional monomers, s...