The intermolecular thiol-ene reaction is emerging as a highly efficient; free-radical mediated "click" process with diverse applications in biofunctionalisation and materials science. The related intramolecular thiol-ene reactions offer significant potential for the preparation of a wide range of sulphur containing heterocycles including synthetic therapeutics such as cyclic peptides and thiosu...

The title compound, C(24)H(30)O(8), was obtained by reaction of ethyl 4-hy-droxy-benzoate with 1,2-dichloro-ethane. The mol-ecule occupies a crystallographic inversion center, with its central ethyl-ene bridge in an anti conformation. The other ethyl-ene bridge has a gauche conformation, with the corresponding O-C-C-O torsion angle being 74.2 (1)°. The benzene rings are almost coplanar with the...

Bicyclo[3.2.0]hept-2-enes undergo thermal rearrangement to norbornenes via diradical transition structures. The synthesis of exo-7-cyclopropylbicyclo[3.2.0]hept-2-ene has been achieved by cycloaddition of cyclopentadiene and cyclopropylketene, generated by treatment of cyclopropylacetyl chloride with triethylamine. A comparison of the cyclopropyl substituent effect with that of other C7 substit...

Bioconjugation based on crosslinking primary amines to carboxylic acid groups has found broad applications in protein modification, drug development, and nanomaterial functionalization. However, proteins, which are made up of amino acids, typically give nonselective bioconjugation when using primary amine-based crosslinking. In order to control protein orientation and activity after conjugation...

The total synthesis of lundurines A-C has been accomplished in racemic and enantiopure forms in 11-13 and 12-14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold(I)-catalyzed alkyne hydroarylation, a cyclopropanation via formal [3 + 2] cycloaddition/nitrogen extrusion, and a remarkable olefin migration ...

The title compound, C(33)H(24)N(4), was prepared by the reaction of a bifunctional aromatic diamine (4,4'-diamino-diphenyl-methane) and an aldehyde (quinoline-2-carboxaldhyde). The mol-ecule consists of two nearly planar (or r.m.s. deviation = 0.017 Å) 4-methyl-N-[(E)-quinolin-2-yl-methyl-idene]aniline moieties, which are linked by the methyl-ene group. The angle between the mean planes of the ...

A metal-free and formal [2 + 2 + 2] cycloaddition of triynes has emerged recently as a novel methodology for the synthesis of fused tricyclic compounds via an intramolecular cascade propargylic ene reaction, Diels-Alder cycloaddition and tautomerization. DFT calculations on three model systems reveal that the ene reaction with low distortion energy makes the metal-free strategy feasible and, as...

We report a highly selective asymmetric ring-closing ene reaction catalysed by aluminum complexes with chiral BINOL. This reaction yields optically active 6-membered cyclized alcohols from unsaturated aldehydes, with good diastereo- and enantioselectivities. Asymmetric amplification of this reaction was investigated by varying the ee of the BINOL employed in the catalyst.

Photoinitiated thiol–ene polymerization was performed in bulk and miniemulsion. We show that the compartmentalization of reaction inside nanodroplets led to faster kinetics yielded polymers with higher molecular weight.

moderate to excellent entantio- and stereoselectivities (ee’s 54-100%) were observed in ple catalyzed hydrolysis of (±)-ethyl 5-oxo-endo-tricyclo[5.2.1.02,6] deca-8-ene-2-carboxylate 5 and the structurally related open chain bicyclic structures (±)-ethyl 3-acetylbicyclo[2.2.1]hept-5-ene-2-carboxylates 7, 9 and (±)-ethyl 3-propanoylbicyclo[2.2.1]hept-5-ene-2-carboxylates 8, 10. a pronounced pref...