Organic chemistry articles from across Nature Portfolio

A highly chemoselective method for the insertion of carbohydrates into existing oligosaccharides has been developed. The reaction sequence involves a selective Lewis-acid catalysed cleavage of one glycosidic bond followed by sequential construction of two new glycosidic bonds.

The idea that three different free radicals could be used together to carry out specific steps in a chemical reaction has long been implausible. A ‘radical sorting’ strategy now achieves this feat to make organic molecules.

d-cyclodextrins are naturally occurring macrocyclic oligosaccharides that act as hosts for hydrophobic guests and are produced on a multi-tonne scale. Now, using chemical synthesis, mirror-image cyclodextrins are produced from l- instead of d-glucose units.

Aminated heteroaromatics are usually synthesized from heteroaromatic substrates. Now, a general photochemical approach that exploits non-aromatic N-heterocyclic ketones as starting materials for the coupling with amines under desaturative catalysis is reported as an alternative.

The development of divergent reaction pathways controlled by different ligands is a critical goal. Here the authors describe a cobalt-catalyzed strategy for cascade coupling of 1,3-enynes with two molecules of acrylates through three reaction modes.

N-Glycosylated heterocycles play important roles in biological systems and drug development, but the synthesis heavily relies on ionic N-glycosylation. Herein, the authors report a dehydroxylative radical method for synthesizing N-glycosides by leveraging copper metallaphotoredox catalysis.

Polarizability, a property that is closely related to softness in the classic theory of Hard and Soft Acids and Bases (HSAB), has been largely overlooked in connecting with enantio-selection in the past. Here, the authors show local polarizability-based electronic effects can rationalize a wide range of stereochemical outcomes in widely-known asymmetric catalytic reactions.

The selective synthesis of ultrahigh-molar-mass (UHMM) cyclic polymers from direct polymerization is elusive. Using a chemically recyclable polythioester as a model, it has now been shown that a common superbase mediates living linear-chain growth, followed by proton-triggered linear-to-cyclic topological transformation, producing UHMM cyclic polymers with a narrow dispersity.

The synthesis of sequence-regulated oligosulfates has not yet been established due to the difficulties in precise reactivity control. Here, the authors report a multi-directional divergent iterative method to furnish oligosulfates based on a chain homologation approach, in which the fluorosulfate unit is regenerated.

A highly chemoselective method for the insertion of carbohydrates into existing oligosaccharides has been developed. The reaction sequence involves a selective Lewis-acid catalysed cleavage of one glycosidic bond followed by sequential construction of two new glycosidic bonds.

The idea that three different free radicals could be used together to carry out specific steps in a chemical reaction has long been implausible. A ‘radical sorting’ strategy now achieves this feat to make organic molecules.

d-cyclodextrins are naturally occurring macrocyclic oligosaccharides that act as hosts for hydrophobic guests and are produced on a multi-tonne scale. Now, using chemical synthesis, mirror-image cyclodextrins are produced from l- instead of d-glucose units.

Coupling an exergonic process with an orthogonal, endergonic one has opened the door to drive artificial systems away from equilibrium. Now, this concept is used to bias the outcome of an uphill chemical reaction.

Chiral amines possessing a stereogenic carbon atom bearing three carbon substituents and one nitrogen substituent are challenging structural motifs to prepare enantioselectively. Now, such motifs have been accessed in high enantiopurities by asymmetric Cu-catalysed propargylic amination using sterically confined ligands.