European Journal of Organic Chemistry

Bisporphyrinoids, thanks to their simplicity and spectral, chemical, and physicochemical properties, have been found to be themost universal and versatile structural motif yet known for investigation of supramolecular chirogenesis.

Addition of 4-alkyl-2-phenyloxazol-5-ones to nitrostyrenes takes place exclusively atthe C-2 position of oxazol-5-one with very high diastereoselectivity

In this study, we have utilized for the first time, a phenoxide ion mediated intramolecular 7-endo-tet ring opening reaction ofsyn-2,3-dihydroxy ester derived cyclic sulfates for the new asymmetric synthesis of 2,3-disubstituted 1-benzoxepines.

Novel green chemistry methods have been developed to install photolabile carbonyl protecting groups. With this advancement, both protection and deprotection of carbonyl compounds can be achieved under neutral conditions without using any other chemical reagents.

A series of macrocyclic azole peptides was synthesized. The investigation of their ability to bind anions in DMSO shows that theses cyclopeptides can act as sensitive and selective receptors for acetate and dihydrogen phosphate anions.

Application of conventional methods of cyclophane chemistry (thiacyclophane formation, sulfone pyrolysis) furnishes [3.2]-, [4.2]-, [4.3]-, and [4.4]paracyclophane, respectively, as well as several derivatives of these hydrocarbons in preparatively satisfactory amounts allowing the study of the chemical properties of these layered aromatic compounds.

The second benzene ring or a carbonyl-containing substituent determine the regioselectivity of electrophilic substitution reactions of [m.n]paracyclophanes. If the bridges contain less than four atoms thenew substituent E is introduced next to the shorter bridge or directly opposite (pseudo-geminally) the directing group. With bridges of four or more atoms, the selectivity breaks down completely.

The 9-mesityl-10-methylacridinium cation in aerated deuterated/normal acetonitrile decomposes to give several side products when continuously exposed to white light. The main breakdown product isolated by column chromatography is identified as3,5-dimethyl-4-(10-methylacridinium)benzaldehyde. This assignment was confirmed by a single-crystal X-ray structure determination.

The genus Ornithogalum consists of garden lily plants indigenous to Southern Africa that contain steroid glycosides with remarkable cytostatic activities. Candicanoside A is a minor congener possessing an unprecedented 24(23→22)abeo-cholestane aglycon.

An annulation reaction of diarylvinylidenecyclopropanes and functionalized aryl halides catalyzed by palladium complexesgives a convenient route to synthesize cyclopropane-containing five-membered heterocyclic derivatives.

The five-step formation of N-[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]-N-methylhydrazine starting with ethanolamine is presented. Moreover, a nitrogen-rich, thermal stable polymer, with a nitrogen content of 33 % was synthesized by using N-[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]-N-methylhydrazine and hexamethylene diisocyanate.

1,3-Dioxolanyl-substituted 1,2-oxazines rearrange under Lewis acidic conditions to provide novel tricyclic products with complex skeleton. Reductive transformations of these tricycles allow the synthesis of a range of enantiopure heterocycles.

A modified Pictet–Spengler reaction has been applied to generate libraries based onthree structural variants of the isocryptolepine alkaloid.