The 1884 suggestion of Pierre Curie (1859–1906) that the type of dissymmetry shown by collinear electric and magnetic fields may induce an enantiomeric excess, in a chemical reaction that would otherwise produce a racemic mixture, is explored i...
The 1,3-dithiolane ring has been recently rehabilitated as a chemical scaffold in drug design. However, for derivatives that are substituted in position 4, the introduction of a chiral center on the heterocycle demands the separation and characteriza...
During the past several years, the frequency of discovery of new molecular entities based on γ- or δ-lactam scaffolds has increased continuously. Most of them are characterized by the presence of at least one chiral center. Herein, we pre...
The couple of chiral sulfur compounds α-lipoic acid (ALA)/α-dihydrolipoic acid (DHALA) has attracted considerable attention in recent years owing to its remarkable anti-inflammatory and antioxidant properties. It is well known that the chirality of t...
Synthetic cathinones, such as 3,4-methylenedioxypyrovalerone (MDPV), are widely abused due to their psychostimulant effects. As they are chiral molecules, studies of their stereochemical stability (racemization can occur in certain temperatures and a...
As a chiral piperidine fungicide, fenpropidin has been widely used to control plant diseases. However, there are rare studies that have investigated fenpropidin at the enantiomer level. In this study, the single-factor analysis combined with a Box-Be...
The determination of natural product stereochemistry plays a significant role in drug discovery and development. Understanding the stereochemistry of natural products is essential for predicting and optimizing their interactions with biological targe...
Sulforaphane is a chiral phytochemical with chemopreventive properties. The presence of a stereogenic sulfur atom is responsible for the chirality of the natural isothiocyanate. The key role of sulfur chirality in biological activity is underscored b...
The paper proposes a putative prebiotic scenario leading to homochirality in the RNA world. In this scenario, racemic ribose, the only chiral moiety in RNA, was enantioseparated (in its pyranose form) on a chiral surface formed by the adsorption of (...
The invariance principle of enzyme enantioselectivity must be absolute because it is absolutely essential to the homochiral biological world. Most enzymes are strictly enantioselective, and tryptophanase is one of the enzymes with extreme absolute en...
Recently, catalytic enantioselective syntheses of N-C axially chiral compounds have been reported by many groups. Most N-C axially chiral compounds prepared through a catalytic asymmetric reaction possess carboxamide or nitrogen-containing aromatic h...
An efficient and facile general method for the synthesis of conduritol C analogs, taking advantage of an enantioselective biocatalysis process of monosubstituted benzenes, is described. The absolute stereochemical patterns of the target molecules (&m...
An organocatalytic enantioselective [3+2] cycloaddition reaction involving 2-arylidene-1,3-indandiones and N-2,2-difluoroethylbenzothiophenone imines was developed. This approach efficiently afforded dispiro[benzothiophenone-indandione-pyrrolidine]s,...
Starting from the enantiopure precursors, a pair of chiral macrocyclic arenes named helic[1]triptycene[3]arenes were conveniently synthesized. The circular dichroism (CD) spectra of the enantiomeric macrocyclic arenes exhibited mirror images, and the...
C2-symmetric diimine generated in situ from (R,R)-HPEN and 8-formylquinoline was readily transformed to novel chiral diimine pre-III bearing 1(S),2(S)-bis(quinolin-8-yl) ethane and salicylic aldehyde fragments via stereoselective diaza-Cope rearrange...
Starting from commercially available ketones, a reproducible and reliable strategy for the synthesis of tetrasubstituted nitroalkenes was successfully developed, using a two-step procedure; the HWE olefination of the ketone to form the corresponding...
We have synthesized a novel chiral NADH model compound, N-methyl-(R)-3-(tert-butyl)-sulphinyl-1,4-dihydropyridine with high enantioselectivity and used it in the reduction of methyl benzoylformate, producing (S)-methyl mandelate in 95% ee. The absolu...
A novel α-tetrazole-substituted 1,1′-binaphthylazepine chiral catalyst has been synthesized and its absolute configuration has been determined by DFT computational analysis of the vibrational circular dichroism (VCD) spectrum of its precu...
Highly efficient asymmetric aldol reactions between α,β-unsaturated keto esters and acyclic ketones catalyzed by chiral diamines are reported. The corresponding products were obtained in excellent yields with excellent enantioselectivities. The absol...
The enantioselective 5-exo-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were general...
A [3 + 2] 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivative...
The enantioselective 1,3-dipolar cycloaddition between imino esters and (Z)-nitroalkenes bearing a masked amino group in the β-position was studied using several chiral ligands and silver salts. The optimized reaction conditions were directly ap...
Due to their structural similarity with natural α-amino acids, α-aminophosphonic acid derivatives are known biologically active molecules. In view of the relevance of tetrasubstituted carbons in nature and medicine and the strong dependence of the bi...
A versatile strategy for the enantioselective synthesis of a benzo[c]oxepine structural core containing natural secondary metabolites was developed. The key steps of the synthetic approach include ring-closing alkene metathesis for seven-member ring...
Oxazaborolidine catalyst (CBS catalyst) has been extensively used for catalytic borane reduction with a predictable absolute stereochemistry and high enantioselectivity. However, the use of isolated CBS catalyst sometimes has the drawback of low repr...
The essential oil and the major non-volatile secondary metabolites from the leaves of Piper subscutatum (Miq.) C. DC. (Family Piperaceae), collected in the Ecuadorian Amazon, were analyzed for the first time in the present study. The essential oil wa...
In this work we report our endeavors toward the development of an asymmetric synthesis of a 3,3-disubstituted isoindolinone, dimethyl 2-(1-methyl-3-oxoisoindolin-1-yl)malonate, via asymmetric cascade reaction of 2-acetylbenzonitrile with dimethylmalo...
Mephedrone, which is one of the most popular synthetic cathinones, has one chiral centre and thus exists as two enantiomers: R-(+)-mephedrone and S-(−)-mephedrone. There are some preliminary data suggesting that the enantiomers of mephedrone ma...
The hydrolase-catalyzed kinetic resolution of fluorinated racemates of 3-arylcarboxylic acids is described. Hydrolysis of ethyl esters of fluorinated acids by esterases and hydrolases in all cases resulted in the formation of hydrolyzed (S)-carboxyli...
In order to design improved chiral ruthenium catalysts for asymmetric olefin metathesis, enantiomeric catalysts incorporating C1-symmetric N-Heterocyclic carbenes (NHC) ligands with syn-related substituents on the backbone were synthesized starting f...
Pyrimidyl alkanol and related compounds were found to be asymmetric autocatalysts in the enantioselective addition of diisopropylzinc to pyrimidine-5-carbaldehyde and related aldehydes. In the asymmetric autocatalysis with amplification of enantiomer...
A novel chiral 1,10-phenanthroline-based fluorescent sensor was designed and synthesized from optical active β-amino acids. It used 1,10-phenanthroline moiety as a fluorescent signaling site and binding site, with optically active β-amino acids as a...
A series of 18 regio- and stereo-chemically diverse chiral non-racemic 1,2-, 1,3-, and 1,4-diamines have been synthesized from commercial (1S)-(+)-ketopinic acid and (1S)-(+)-10-camphorsulfonic acid. The structures of the diamines are all based on th...
Chiral natural product molecules are generally assumed to be biosynthesized in an enantiomerically pure or enriched fashion. Nevertheless, a significant amount of racemates or enantiomerically enriched mixtures has been reported from natural sources....
This feature article gives a general introduction to the phenomenon of supramolecular chirogenesis using the most representative examples of different chirogenic assemblies on the basis of ethane-bridged bis-porphyrinoids. Supramolecular chirogenesis...
Heterocyclic compounds play an important role in medicinal chemistry and occupy a central position in synthetic organic chemistry. Both benzofuran and benzothiophene are considered as very important structures due to their diverse biological and pha...
The main objective of this study is the enantioselective synthesis of carboxyhydroxyphosphonates by lipase-catalyzed reactions. For this purpose, racemic dimethyl and dibutyl 1-butyryloxy-1-carboxymethylphosphonates were synthesized and hydrolyzed, u...
Amanita hemibapha subsp. javanica (Amanitaceae) is an edible Korean wild mushroom. A. hemibapha subsp. javanica is often confused with A. subjunquillea, known as the East Asian death cap, which is potentially fatal when ingested. This study aimed to...
Lagunamide D, a new cytotoxic macrocyclic depsipeptide, was discovered from a collection of marine cyanobacteria from Loggerhead Key in the Dry Tortugas, Florida. An intramolecular ester exchange was observed, where the 26-membered macrocycle could c...
To develop potent and safer analgesics, we designed and synthesized a novel enantiomerically enriched ethereal analog of (R)-iso-moramide, namely 2-[(2R)-2-(morpholin-4-yl)propoxy]-2,2-diphenyl-1-(pyrrolidin-1-yl)ethan-1-one. The titled active agent...
Crystal structure prediction is based on the assumption that the most thermodynamically stable structure will crystallize first. The existence of other structures such as polymorphs or from counterenantiomers requires an accurate calculation of the e...
A series of new benzofuryl α-azole ketones was synthesized and reduced by asymmetric transfer hydrogenation (ATH). Novel benzofuryl β-amino alcohols bearing an imidazolyl and triazolyl substituents were obtained with excellent enantioselec...
Tetrahydroprotoberberine alkaloids (THPBs) are bioactive natural products bearing stereogenic centers that frequently exhibit enantiomer-specific pharmacological effects. Xylopinine (XPN), a representative THPB, shows cytotoxic, antimicrobial, and an...
Aflatoxins are carcinogenic mycotoxins that are produced by the filamentous fungus Aspergillus flavus, a contaminant of numerous food crops. Aflatoxins are synthesised via the aflatoxin biosynthesis pathway, with the enzymes involved encoded by the a...