http://www.cell.com/article/S2666389922002069/pdf

SELFIES and the future of molecular string representations

We report herein an efficient approach for the enantioselective synthesis of inherently chiral calix[4]arenes via palladium-catalyzed asymmetric intramolecular C-H arylations. Using a chiral bifunctional phosphine-carboxylate ligand, the inherent chirality on macrocyclic scaffolds was induced successfully, from which a wide range of calix[4]arenes with fluorenone motifs were obtained with good yields and excellent enantioselectivities (up to >99% ee). The synthetic utility of this method was demonstrated by diverse transformations of the products, thus substantially expanding the chemical space of chiral calix[4]arenes. Further investigations of photophysical and chiroptical properties revealed that calix[4]arenes bearing two fluorenone moieties displayed remarkable glum values (up to 0.019), highlighting the great potential of inherent chirality in the development of organic optoelectronic materials.

Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Palladium-Catalyzed Asymmetric Intramolecular C-H Arylations.

An efficient approach for asymmetric synthesis of planar-chiral macrocycles (paracyclophanes) has been disclosed through enantioselective electrophilic aromatic aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. A wide range of chiral macrocycles bearing varied ring sizes (16 to 23-membered) and functional group-containing ansa chains were readily afforded using this method, with excellent yields and high enantioselectivities (23 examples, up to 99.5:0.5 er). Experimental studies and DFT calculations were performed to elucidate the mechanism and origin of stereoselectivities of these reactions. Preliminary utilization of the planar-chiral macrocycle as chiral organocatalyst showcased the potential applications of these novel chiral skeletons.

Enantioselective Synthesis of Planar-Chiral Macrocycles through Asymmetric Electrophilic Aromatic Amination.

Abstract We report our investigation of the utility of peptide crosslinking cytochrome P450 enzymes from biarylitide biosynthesis to generate a range of cyclic tripeptides from simple synthons. The crosslinked tripeptides produced by this P450 include both tyrosine‐histidine (A−N−B) and tyrosine‐tryptophan (A−O−B) crosslinked tripeptides, the latter a rare example of a phenolic crosslink to an indole moiety. Tripeptides are easily isolated following proteolytic removal of the leader peptide and can incorporate a wide range of amino acids in the residue inside the crosslinked tripeptide. Given the utility of peptide crosslinks in important natural products and the synthetic challenge that these can represent, P450 enzymes have the potential to play roles as important tools in the generation of high‐value cyclic tripeptides for incorporation in synthesis, which can be yet further diversified using selective chemical techniques through specific handles contained within these tripeptides.

Cytochrome P450Blt Enables Versatile Peptide Cyclisation to Generate Histidine‐ and Tyrosine‐Containing Crosslinked Tripeptide Building Blocks

Planar chirality is one of the most fascinating expressions of chirality, which is exploited by nature to lock three-dimensional chiral conformations and, more recently, by chemists to create new chiral reagents, catalysts, and functional organic materials. Nevertheless, the shortage of procedures able to induce and secure asymmetry during the generation of these unique chiral entities has dissuaded chemists from exploiting their structural properties. This Minireview intends to illustrate the limited but remarkable catalytic methods that have been reported for the production of planar chirality in strained molecules and serve as a source of inspiration for the development of new unconventional procedures, which are expected to appear in the near future. 

http://addi.ehu.es/bitstream/10810/56014/1/Angew%20Chem%20Int%20Ed%20-%202021%20-%20L%20pez%20-%20Planar%20Chirality%20A%20Mine%20for%20Catalysis%20and%20Structure%20Discovery.pdf

Planar Chirality: A Mine for Catalysis and Structure Discovery

We introduce a Maxwell demon which generates many-body entanglement robustly against bit-flip noises, which allows us to obtain quantum advantage. Adopting the protocol of the voter model used for opinion dynamics approaching consensus, the demon randomly selects a qubit pair and performs a quantum feedback control, in continuous repetitions. We derive upper bounds of the entropy reduction and the work extraction rates by demon's operation, which are determined by a competition between the quantum-classical mutual information acquired by the demon and the absolute irreversibility of the feedback control. Our finding of the upper bounds corresponds to a reformulation of the second law of thermodynamics under a class of Maxwell demon which generates many-body entanglement in a working substance. 

Quantum consensus dynamics by entangling Maxwell demon

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Planar Chirality: A Mine for Catalysis and Structure Discovery

Quantum consensus dynamics by entangling Maxwell demon