Substitution Of Hydrogen Atoms Research Articles

Synthesis, crystals structures, DFT, and anticancer activities of polycyclic heterocyclic quinones

In this work, we synthesized six polycyclic heterocyclic quinones (PHQs) and one unexpected product (compound 6). We verified all of their structures by 1HNMR, 13CNMR, and HRMS and obtained four crystal structures of the seven products. At first, we compared the crystal structures with crystal structures similar to those reported in the literature and explained their differences by conjugative effect, hyperconjugative effect, and electrostatic effect. Then, we compared the crystal structure of compound 6 with the calculated structure of compound 6. The natural bond orbital analysis showed that the calculated structure formed intramolecular hydrogen bonds, whereas the crystal structure formed intermolecular hydrogen bonds but not intramolecular hydrogen bonds. The main reason for this difference was not due to the atomic charge or the interatomic distance, but rather the energy levels of the orbitals of the lone-pair electrons. In crystal structures, the intermolecular interactions contained many weak interactions, and we used the hydrogen atom substitution (HAS) method to divide the total intermolecular interactions as several independent weak interactions and to calculate their energies. The HAS method was often successful if the substituted group did not have a strong effect on the electronic structure of the entire molecule, and we found examples in the calculations of energies of weak interactions of crystal structure of compound 6 and compound 3a. An unsuccessful example of the HAS method was the substitution of C = O group with CH2 group to eliminate the O…H-N hydrogen bond interaction from the total interaction. According to the HAS method, our calculations showed that the strength order of the weak interactions was as follows: π-π stacking > hydrogen bond > n-π stacking > σ-π stacking. For the hydrogen bond, the strength order was as follows: C = O…H-N > CCl…H-N > C-F…H-N. For n-π stacking interaction, the strength order was as follows: Cl-π > N-π > F-π. Finally, we selected five synthesized PHQs to test anticancer activities and some of them showed better anticancer activities than the positive control drugs.

Improvements of the increase of selenium-modified rate on the structural characteristics and antioxidant properties of Lycium barbarum polysaccharides by subcritical water method

Effects of the increase of the selenium-modified rate on the structural characteristics and antioxidant abilities of the selenized polysaccharides (Se-PS) were seldom reported. In this work, LBP1-1 purified from Lycium barbarum polysaccharides (LBP) was selenized by the subcritical water (SW) versus the traditional hot water (HW) method to obtain Se-modified SW-SeLBP1-1 and HW-SeLBP1-1, respectively. The results revealed that SW-SeLBP1-1 contained 17.49 ± 0.35 mg Se/g, significantly higher than 5.68 ± 0.05 mg/g of HW-Se-LBP1-1 and the reported before. The selenization time was reduced from 7 h to 20 min. Se modifications were mainly achieved by Se substitutions of hydrogen atoms in hydroxyl groups of LBP1-1. Xylose and galactose in LBP1-1 could be easily and regularly modified by Se, the Se modifications of the other monosaccharides showed significant different between the two methods. The generated C-O-Se groups could readily make SW-SeLBP1-1 formed a more orderly network structure than that of HW-SeLBP1-1 when Se-modified rate increased 11.81 %, resulting in its antioxidant activities increasing over 17.3 % in vitro.

Two-step synthesis of indeno[1,2-b]furazanopyrazines through combination of the SNH and Heck reactions

Enamines generated in situ from aliphatic amines and acetone react with 5-(2-bromophenyl)furazano[3,4-b]pyrazines via the nucleophilic substitution of hydrogen atom of the pyrazine ring. A representative of 9H-indeno[1,2-b]furazanopyrazin-9-ylidene ring system has been accessed by exploiting the intramolecular Heck cyclization of the obtained SNH-product. Several compounds derived from the SNH reaction, namely, N-alkyl-1-[6-(2-bromophenyl)furazano[ 3,4-b]pyrazin-5-yl]prop-1-en-2-amines, proved to exhibit a bacteriostatic activity in vitro against Mycobacterium tuberculosis H37Rv

Decaborane: From Alfred Stock and Rocket Fuel Projects to Nowadays.

The review covers more than a century of decaborane chemistry from the first synthesis by Alfred Stock to the present day. The main attention is paid to the reactions of the substitution of hydrogen atoms by various atoms and groups with the formation of exo-polyhedral boron-halogen, boron-oxygen, boron-sulfur, boron-nitrogen, boron-phosphorus, and boron-carbon bonds. Particular attention is paid to the chemistry of conjucto-borane anti-[B18H22], whose structure is formed by two decaborane moieties with a common edge, the chemistry of which has been intensively developed in the last decade.

Cation recognition controlled by protonation or chemical reduction: a computational study.

To control biochemical processes, non-covalent interactions involving cations are activated by protons or electrons. In the present study, the bonding situation between: (i) carboxylic acid or (ii) ferrocene-functionalized crown ether derivatives and cations (Li+, Na+ or K+) has been elucidated and, mainly, tuned by the substitution of hydrogen atoms by electron donor (-NH2) or acceptor (-NO2) groups. The deprotonation of the carboxyl groups improves the interaction with the cations through more favorable electrostatic O⋯cation interactions. Reducing the ferrocene structures favors cationic recognition supported by a less unfavorable iron⋯cation binding. The receptors preferably interact with smaller cations because of more attractive electrostatic and orbital (σ or π) O⋯cation interactions. The presence of electron donor or acceptor groups in the carboxylic acid-functionalized crown ethers promotes less attractive interactions with the cations, mainly due to the less favorable electrostatic O⋯Na+ interactions. The -H → -NH2 substitution in the ferrocene framework favors the cationic recognition. It is based on the strengthening of the electrostatic and σ O⋯Na+ and H2N⋯Na+ bonds. The (i) absence of repulsive electrostatic iron⋯cation interactions, or (ii) the presence of oxygen atoms with large electron density, ensures carboxylic acid-functionalized crown ethers have more favorable interactions with cations than ferrocene compounds. Therefore, this work has demonstrated how cation recognition can be improved by structural changes in carboxylic acid- or ferrocene-functionalized crown ethers and has shown that the carboxylic acid molecules appear to be better candidates for cation recognition than ferrocene derivatives.

Nature of Beryllium, Magnesium, and Zinc Bonds in Carbene⋯MX2 (M = Be, Mg, Zn; X = H, Br) Dimers Revealed by the IQA, ETS-NOCV and LED Methods.

The nature of beryllium−, magnesium− and zinc−carbene bonds in the cyclopropenylidene⋯MX2 (M = Be, Mg, Zn; X = H, Br) and imidazol-2-ylidene⋯MBr2 dimers is investigated by the joint use of the topological QTAIM-based IQA decomposition scheme, the molecular orbital-based ETS-NOCV charge and energy decomposition method, and the LED energy decomposition approach based on the state-of-the-art DLPNO-CCSD(T) method. All these methods show that the C⋯M bond strengthens according to the following order: Zn < Mg << Be. Electrostatics is proved to be the dominant bond component, whereas the orbital component is far less important. It is shown that QTAIM/IQA underestimates electrostatic contribution for zinc bonds with respect to both ETS-NOCV and LED schemes. The σ carbene→MX2 donation appears to be much more important than the MX2→ carbene back-donation of π symmetry. The substitution of hydrogen atoms by bromine (X in MX2) strengthens the metal−carbene bond in all cases. The physical origin of rotational barriers has been unveiled by the ETS-NOCV approach.

On the Coexistence of the Carbene⋯H-D Hydrogen Bond and Other Accompanying Interactions in Forty Dimers of N-Heterocyclic-Carbenes (I, IMe2, IiPr2, ItBu2, IMes2, IDipp2, IAd2; I = imidazol-2-ylidene) and Some Fundamental Proton Donors (HF, HCN, H2O, MeOH, NH3).

The subject of research is forty dimers formed by imidazol-2-ylidene (I) or its derivative (IR) obtained by replacing the hydrogen atoms in both N-H bonds with larger important and popular substituents of increasing complexity (methyl = Me, iso-propyl = Pr, tert-butyl = Bu, phenyl = Ph, mesityl = Mes, 2,6-diisopropylphenyl = Dipp, 1-adamantyl = Ad) and fundamental proton donor (HD) molecules (HF, HCN, HO, MeOH, NH). While the main goal is to characterize the generally dominant C⋯H-D hydrogen bond engaging a carbene carbon atom, an equally important issue is the often omitted analysis of the role of accompanying secondary interactions. Despite the often completely different binding possibilities of the considered carbenes, and especially HD molecules, several general trends are found. Namely, for a given carbene, the dissociation energy values of the IRHD dimers increase in the following order: NH< HO < HCN ≤ MeOH ≪ HF. Importantly, it is found that, for a given HD molecule, IDipp forms the strongest dimers. This is attributed to the multiplicity of various interactions accompanying the dominant C⋯H-D hydrogen bond. It is shown that substitution of hydrogen atoms in both N-H bonds of the imidazol-2-ylidene molecule by the investigated groups leads to stronger dimers with HF, HCN, HO or MeOH. The presented results should contribute to increasing the knowledge about the carbene chemistry and the role of intermolecular interactions, including secondary ones.

Preparation of multi-element doped porous carbon by microwave cross-linking stabilization of disposable surgical masks and its electrochemical properties as sulfur loading

Numerous disposable surgical masks (DSMs) were consumed with the development of COVID-19 epidemic. Non-solid products recovered by pyrolysis is more than twenty species with low added value. Therefore, the search for a reasonable carbonization method can not only alleviate the pressure of global plastic pollution, but also produce considerable economic value. Here it is found that microwave cross-linking can promote the substitution of hydrogen atom in the polymer master chain of DSMs by hydrogen atom, which can reorganize the easily cracked DSMs into sp2-hybridized aromatic carbon, it can maintain 51.2 % carbon yield at1000 ℃. The difference between the DSMs-based porous carbon obtained by in-situ and post-processing N doping was further compared, and it was found that the specific surface area of the activated in-situ doped sample (P-SNO@DSMs) was as high as 2278 m2·g−1, which had rich hierarchical pore structure and high heteroatoms doping rate. Benefiting from the synergistic effect of heteroatoms and hierarchical holes, P-SNO@DSMs sulfur cathode delivers a high specific capacity of 1550 mAh·g−1 at 0.1 C and exhibits excellent long-term cycling performance with the smaller capacity decay of 0.13 % per cycle after 400 cycles. In this work, clean and efficient microwave cross-linking not only realized the efficient recovery of waste DSMs, but also the application of the prepared materials can be broadened by adding additional heteroatomic sources in the process of microwave cross-linking.

Effect of fluorine substitution on the photobiological and electronic properties of resveratrol crystal structure: A first- principles study

The electrical and optical properties of pure resveratrol (RS) and RS derivatives from substituted fluorine atom at hydrogen sites (fluorine is bonded to an oxygen or a carbon atom) are investigated by first-principles calculations. It is shown that RS is a semiconductor with an indirect bandgap of 2.47 eV. The substitution of hydrogen atoms by fluorine atoms that is bonded to oxygen atom changes the bandgap value and affect significantly on optical properties of RS. For other derivatives, the hydrogen substitution by fluorine does not change the bandgap value sensibility. The nature of band gap change from indirect to direct at F3 structure. Optical spectra of F3 to F8 derivatives are very similar to RS. Birefringenceis observed in all RS derivatives. The results show that fluorine atoms play key role in photo biological applications of RS derivatives.

Front Cover: Bromine Substitution of Organic Modifiers Fixed on a Titanium(IV) Oxide Photocatalyst: A New Strategy Accelerating Visible Light‐Induced Hydrogen‐Free Hydrogenation of Furfural to Furfuryl Alcohol (ChemCatChem 5/2022)

The Front Cover shows chemoselective hydrogenation of furfural (FAL) to furfuryl alcohol (FOL) over nine kinds of organically modified TiO2 (OM/TiO2’s) under irradiation of visible light without the use of hydrogen gas (H2). In their Full Paper, Y. Yamamoto et al. show that all OM/TiO2’s produced FOL and a linear relation between the reaction rate and amount of FAL adsorbed on the OM/TiO2’s was observed. Among them, OM/TiO2’s having bromine (Br)-substituted 2,3-naphthalenediol (NDO) exhibited larger reaction rates and the rate increased with an increase in the number of Br groups. These results revealed that substitution of hydrogen atoms of organic modifiers with Br is a simple but effective method for increasing the photocatalytic activity. The explored 1,4,6-tribromo-2,3-NDO-modified TiO2 also showed a high performance in H2-free chemoselective reduction of benzaldehydes having reducible groups to corresponding benzyl alcohols. More information can be found in the Full Paper by Y. Yamamoto et al.

Hyperspectral CARS microscopy and quantitative unsupervised analysis of deuterated and non-deuterated fatty acid storage in human cells.

Coherent anti-Stokes Raman scattering (CARS) implemented as a vibrational micro-spectroscopy modality eradicates the need for potentially perturbative fluorescent labeling while still providing high-resolution, chemically specific images of biological samples. Isotopic substitution of hydrogen atoms with deuterium introduces minimal change to molecular structures and can be coupled with CARS microscopy to increase chemical contrast. Here, we investigate HeLa cells incubated with non-deuterated or deuterium-labeled fatty acids, using an in-house-developed hyperspectral CARS microscope coupled with an unsupervised quantitative data analysis algorithm, to retrieve Raman susceptibility spectra and concentration maps of chemical components in physically meaningful units. We demonstrate that our unsupervised analysis retrieves the susceptibility spectra of the specific fatty acids, both deuterated and non-deuterated, in good agreement with reference Raman spectra measured in pure lipids. Our analysis, using the cell-silent spectral region, achieved excellent chemical specificity despite having no prior knowledge and considering the complex intracellular environment inside cells. The quantitative capabilities of the analysis allowed us to measure the concentration of deuterated and non-deuterated fatty acids stored within cytosolic lipid droplets over a 24 h period. Finally, we explored the potential use of deuterium-labeled lipid droplets for non-invasive cell tracking, demonstrating an effective application of the technique for distinguishing between cells in a mixed population over a 16 h period. These results further demonstrate the chemically specific capabilities of hyperspectral CARS microscopy to characterize and distinguish specific lipid types inside cells using an unbiased quantitative data analysis methodology.

Bromine Substitution of Organic Modifiers Fixed on a Titanium(IV) Oxide Photocatalyst: A New Strategy Accelerating Visible Light‐Induced Hydrogen‐Free Hydrogenation of Furfural to Furfuryl Alcohol

AbstractTitanium(IV) oxide (TiO2) modified with 2,3‐naphthalenediol (NDO) works as a photocatalyst for some reactions under irradiation of visible light. We prepared and characterized nine kinds of organically modified TiO2 (OM/TiO2) and used OM/TiO2 for chemoselective hydrogenation of furfural (FAL) to furfuryl alcohol (FOL) under irradiation of visible light without the use of hydrogen gas. All OM/TiO2 prepared in this study produced FOL and a linear relation between the reaction rate and amount of FAL adsorbed on the OM/TiO2 was observed. Among them, OM/TiO2 having bromine (Br)‐substituted NDO exhibited larger reaction rates and the rate increased with an increase in the number of Br groups. In the case of the most active 1,4,6‐tribromo‐2,3‐naphthalenediol‐modified TiO2 (TB‐NDO/TiO2), the reaction rate was not dependent on the amount of TB‐NDO and the photoabsorption of TB‐NDO/TiO2 but was dependent on the amount of FAL adsorbed on TB‐NDO/TiO2. These results revealed that substitution of hydrogen atoms of organic modifiers with Br is a simple but effective method for increasing the photocatalytic activity. The explored TB‐NDO/TiO2 also showed high performance in H2‐free chemoselective reduction of benzaldehydes having reducible groups to corresponding benzyl alcohols.

Computational Design of New N-Heterocyclic Silyl Pincer Fullerenes

A density functional theory study was performed to design new N-heterocyclic silyl pincer fullerenes based on the reactions of diaminofullerene with chlorosilanes SiHRCl2. Reaction energies of the formation of pincer fullerene ligands increased through the substitution of flanking arms with CH3 and phenyl groups. However, substituting hydrogen of SiH2 with methyl slightly increased the corresponding reaction energies; replacing hydrogen with phenyl group decreased the reaction energies of the considered pincer fullerenes. While the calculated electrophilicity values of the pincer fullerenes are larger than the electrophilicity values obtained for the fullerene derivatives, the substitution of hydrogen atoms of central SiH2 and PH2 did not has a noticeable impact on the electrophilicity values of the pincer fullerenes. The only exception was SiHPh(NCH2PH2)2C60. Natural bonding orbital analysis showed that the delocalization of electrons from the lone pairs of phosphorous atoms to the n* orbital of transition metal atoms was a key factor for stabilizing the considered complexes. The strongest interaction was due to the delocalization of electrons from lone pairs of phosphorous atoms in the flanking arms to the LP* of transition metals, which was followed by the delocalization of electrons of the Si-H σ* orbitals to the LP* of transition metals.

Synthesis, structures, DFT calculations, and Hirshfeld surface analysis of sulfonium derivatives of the closo-decaborate anion [B10X9-cyclo-S(CH2)4]– and [B10X9-cyclo-S(CH2CH2)2O]– (X = H, Cl, Br)

This work is devoted to the synthesis and modification of sulfur-containing derivatives of the closo-decaborate anion with cyclic substituents [2–B10H9–cyclo–S(CH2)4]–(1) and [2–B10H9-cyclo-S(CH2CH2)2O]–(2). Their perhalogenated analogs [2–B10Cl9–cyclo–S(CH2)4]–(3), [2–B10Cl9-cyclo-S(CH2CH2)2O]–(4), [2–B10Br9–cyclo–S(CH2)4]–(5), and [2–B10Br9-cyclo-S(CH2CH2)2O]–(6) were synthesized. The obtained compounds were investigated by 11B, 1H, and 13C NMR spectroscopy and single crystal X-ray diffraction. The analysis of Hirshfeld surfaces and quantum-chemical calculations by the DFT method made it possible to establish the contribution of various intermolecular contacts to the crystal packing of compounds 1–6 and to study the effect of substitution of hydrogen atoms in the boron cage on the strength of the B–S bond.

Acid-Catalyzed Hydrothiolation of gem-Difluorostyrenes to Access α,α-Difluoroalkylthioethers.

The substitution of hydrogen atoms with fluorine in bioactive molecules can greatly impact physicochemical, pharmacokinetic, and pharmacodynamic properties. However, current synthetic methods cannot readily access many fluorinated motifs, which impedes utilization of these groups. Thus, the development of new methods to introduce fluorinated functional groups is critical for developing the next generation of biological probes and therapeutic agents. The synthesis of one such substructure, the α,α-difluoroalkylthioether, typically requires specialized conditions that necessitate early-stage installation. A late-stage and convergent approach to access α,α-difluoroalkylthioethers could involve nucleophilic addition of thiols across gem-difluorostyrenes. Unfortunately, under basic conditions, nucleophilic addition to gem-difluorostyrenes generates an anionic intermediate that can undergo facile elimination of fluoride to generate α-fluorovinylthioethers. To overcome this decomposition, we herein exploit an acid-based catalyst system to facilitate simultaneous nucleophilic addition and protonation of the unstable intermediate. Ultimately, the optimized mild conditions afford the desired α,α-difluoroalkylthioethers in high selectivity and moderate to excellent yields. These α,α-difluoroalkylthioethers are less nucleophilic and more oxidatively stable relative to nonfluorinated thioethers, suggesting the potential application of this unexplored functional group in biological probes and therapeutic agents.

Effect of Substitution of Hydrogen Atoms in the Molecules of Anthrone and Anthraquinone.

The geometry of anthrone and anthraquinone—natural substances of plant origin—was investigated under the substitution of hydrogen atoms in side aromatic ring and, for anthrone, also in the central ring. A significant influence of substitution on geometry expressed by the angle between the side rings was shown. The geometry changes are connected with the changes of electron density and aromaticity of the anthrone and anthraquinone rings. The flexibility of the investigated compounds was confirmed by comparison of the optimized molecules and the molecules in the crystal state where the packing forces can influence the molecular geometry.

New promising proton conducting electrolyte for high-temperature fuel cells based on hydrophobic guanidine salt

Guanidine salts are promising proton conductors due to the high content of dissociable protons in guanidinium cation that ensure an efficient proton transfer along hydrogen-bonded network formed by proton donor and proton acceptor sites. However, the high melting point of most guanidine salts is a serious drawback for their application as proton conducting electrolytes. Reducing the symmetry of guanidinium cations by the substitution of hydrogen atoms on alkyl radicals reduces the melting points but also leads to decreased proton conductivity. In this study, monosubstituted guanidine salt, N-butylguanidinium bis(trifluoromethylsulfonyl)imide (BG-TFSI), has been synthesized by a simple two-step method. It is water immiscible room temperature protic ionic liquid. The structure of BG-TFSI was confirmed by nuclear magnetic resonance spectroscopy, as well as infrared spectroscopy. According to thermal gravimetric analysis data, the ionic liquid has the thermal degradation point (5% weight loss) of 348 °C which indicates its excellent thermal stability for use in high-temperature fuel cells. The ionic conductivity of BG-TFSI determined by the electrochemical impedance method was found to be 9·10-4 S/cm at room temperature. This value increased by almost one order of magnitude above 100 °C thus reaching an acceptable level for use in fuel cells. The activation energy Ea calculated from the Arrhenius plot for BG-TFSI is found to be 16.4 kJ/mol which is similar to those reported for other guanidine salts. Based on the obtained results one can assume that the proton transport in BG-TFSI is dominated by Grotthus-type (hopping) mechanism. The results of this study indicated that BG-TFSI is a promising proton conducting electrolyte for fuel cells operating at elevated temperatures in water-free conditions. The hydrophobicity of the ionic liquid is an important advantage since it can prevent its leaching from the polymer electrolyte membrane during the operation of a fuel cell.

Thermal stability and detonation character of nitroso-substituted derivatives of cubane

ABSTRACT A series of derivatives of nitroso-substituted cubane were designed through the substitution of hydrogen atoms by nitroso groups one by one. The heats of formation (HOFs) were calculated to explore the thermal stability. The bond dissociation energies (BDEs) and the bond orders of the trigger bonds were also investigated to explore the molecular stability kinetically. Furthermore, the steric effect was confirmed as the determinant of molecular stability for title molecules. To explore the detonation properties, the detonation pressure (P), the detonation velocity (D), the heat of detonation (Q), and the specific density (ρ) were calculated by using the empirical Kamlet-Jacobs (K-J) equations. To predict the sensitivity, the characteristic drop height (H 50) is calculated. Based on our calculations, the octanitrosocubane is found with detonation parameters (D = 9.03 km/s, P = 36.96 GPa) better than that of RDX with enough stability.

A confocal Raman microscopic visualization of small penetrants in cellulose acetate using a deuterium-labeling technique

The purpose of the present study was to visualize the sorption dynamics of small compounds, such as propylene glycol (PG) in cellulose acetate (CA) film, by deuterium (d) labeling-aided confocal Raman spectroscopy (CRM). Substitution of hydrogen atoms in the target molecule with deuterium caused a marked shift of C-H bond-related Raman bands to low wavenumbers, while the number of deuterium did not affect the magnitude of the shift. Raman bands derived from the stretching vibration of C–H near 2900 cm−1 for PG and ethanol were shifted to approximately 2100 cm−1 for PG-d6 and ethanol-d5 in the silent region of the CA Raman spectrum. When PG-d6 was dissolved in glycerol triacetate (GTA), the observed Raman intensity ratio at 2123 cm−1 of PG-d6 against 1739 cm−1 of GTA (C=O bond-related) showed a linear relationship between the molar and intensity ratios, indicating that the observed Raman intensity can be used for quantitative assay of the target in polymer film. The depth profiling experiments by CRM revealed that the distribution (or sorption) of PG-d6 in CA film was successfully visualized as a function of Raman band at the characteristic 2123 cm−1 intensity ratio.

Гидроксипроизводные левоглюкозенона в реакциях энантиоселективного восстановления 1,3-дифенилпропан-1-она

The enantioselective reduction of prochiral ketones is an important method for the preparation of enanti-enriched secondary alcohols, which can serve as starting materials for optically active compounds. Chiral metal hydride reagents, such as lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4), modified with chiral ligands, have been developed to effect enantioselective reduction. However, in most cases, derivatives are used to obtain chiral hydride reagents, which are rare and hardly available. Therefore, the search for more accessible and effective derivatives suitable for the modification of hydride reagents is an urgent task. Levoglucosenone is an optically pure enone of carbohydrate nature, readily available by pyrolysis of any cellulose-containing materials. Levoglucosenone is considered a promising bioplatform for both laboratory synthesis and industrial use. The prospect of the development of chemistry of levoglucosenone and its derivatives in industry makes it possible to pay attention to these compounds from the point of view of studying their possibilities as chiral inducers or auxiliaries. In this work, we studied the possibilities of chiral induction in the reduction reactions of 1,3-diphenylpropan-1-one with hydride reagents obtained by replacing hydrogens in LiAlH4 and NaBH4 with hydroxy derivatives of levoglucosenone. The reduction of 1,3-diphenylpropan-1-one with chiral aluminum hydride reagents proceeded with low enantioselectivity, mainly with a predominance of (S)-1,3-diphenylpropan-1-ol. It was found that the enantiomeric purity of the S-stereomer decreases with an increase in the substitution of hydrogen atoms in LiAlH4 by hydroxy derivatives of levoglucosenone. Reduction of 1,3-diphenylpropan-1-one with reagents obtained by partial neutralization of NaBH4 with hydroxy derivatives of levoglucosenone, on the contrary, predominantly leads to the formation of (R)-1,3-diphenylpropan-1-ol. The addition of AcOH and Bu4NCl to NaBH4 has a positive effect on the optical frequency of the R-alcohol. At the same time, enantioselectivity in the reactions was almost absent upon reduction of 1,3-diphenylpropan-1-one with reagents obtained by partial neutralization of BH3. The best results of enantioselective reduction were shown by unsaturated alcohols: (1S,4S,5R) -6,8-dioxabicyclo[3.2.1]oct-2-en-4-ol and (1S,4S,5R)-4-methyl-6,8-dioxabicyclo[3.2.1]oct-2-en-4-ol, of which (1S,4S,5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-ol was the most effective. It is likely that an increase in the enantioselectivity of reactions carried out in the presence of hydroxy derivatives of levoglucosenone is possible by obtaining more bulky chiral ligands, provided that the double bond is retained.