5,291 results match your criteria enantioselectivity chiral


Remote Amino Acid Recognition Enables Effective Hydrogen Peroxide Activation at a Manganese Oxidation Catalys.

Angew Chem Int Ed Engl 2021 Dec 1. Epub 2021 Dec 1.

Universitat de Girona, Institut de Química Computacional i Catàlisi, SPAIN.

Precise delivery of a proton plays a key role in O 2 activation at iron oxygenases, enabling the crucial O-O cleavage step that generates the oxidizing high valent metal-oxo species. Such proton is delivered by acidic residues that may either directly bind the iron center or lie in its second coordination sphere. Herein, a supramolecular strategy for enzyme-like H 2 O 2 activation at a biologically inspired manganese catalyst, with nearly stoichiometric amount (1-1. Read More

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December 2021

Rational Design of Axially Chiral Styrene-Based Organocatalysts and Their Application in Catalytic Asymmetric (2+4) Cyclizations.

Angew Chem Int Ed Engl 2021 Nov 30. Epub 2021 Nov 30.

Jiangsu Normal University, School of Chemistry and Chemical Engineering, Tongshan New District, Shanghai Road 101, 221116, Xuzhou, CHINA.

A new class of axially chiral styrene-based thiourea-tertiary amine catalysts, which have unique characteristics such as an efficient synthetic route, multiple chiral elements and multiple activating groups, has been rationally designed. These new chiral catalysts have proven to be efficient organocatalysts, enabling the chemo-, diastereo- and enantioselective (2+4) cyclization of 2-benzothiazolimines with homophthalic anhydrides in good yields (up to 96%) with excellent stereoselectivities (all >95:5 dr, up to 98% ee). More importantly, theoretical calculations elucidated the important role of axially chiral styrene moiety in controlling both the reactivity and the enantioselectivity. Read More

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November 2021

Chiral Aminoalcohols and Squaric Acid Amides as Ligands for Asymmetric Borane Reduction of Ketones: Insight to In Situ Formed Catalytic System by DOSY and Multinuclear NMR Experiments.

Molecules 2021 Nov 14;26(22). Epub 2021 Nov 14.

Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Bl. 9, Acad. G. Bonchev Str., 1113 Sofia, Bulgaria.

A series of squaric acid amides (synthesized in 66-99% isolated yields) and a set of chiral aminoalcohols were comparatively studied as ligands in a model reaction of reduction of α-chloroacetophenone with BH•SMe. In all cases, the aminoalcohols demonstrated better efficiency (up to 94% ), while only poor asymmetric induction was achieved with the corresponding squaramides. A mechanistic insight on the in situ formation and stability at room temperature of intermediates generated from ligands and borane as possible precursors of the oxazaborolidine-based catalytic system has been obtained by H DOSY and multinuclear 1D and 2D (H, B, C, N) NMR spectroscopy of equimolar mixtures of borane and selected ligands. Read More

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November 2021

Enantioselectivity of Chiral Derivatives of Xanthones in Virulence Effects of Resistant Bacteria.

Pharmaceuticals (Basel) 2021 Nov 10;14(11). Epub 2021 Nov 10.

Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal.

Antimicrobial peptides are one of the lines of defense produced by several hosts in response to bacterial infections. Inspired by them and recent discoveries of xanthones as bacterial efflux pump inhibitors, chiral amides with a xanthone scaffold were planned to be potential antimicrobial adjuvants. The chiral derivatives of xanthones were obtained by peptide coupling reactions between suitable xanthones with enantiomerically pure building blocks, yielding derivatives with high enantiomeric purity. Read More

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November 2021

Enantioselective bioaccumulation and toxicity of the novel chiral antifungal agrochemical penthiopyrad in zebrafish (Danio rerio).

Ecotoxicol Environ Saf 2021 Nov 23;228:113010. Epub 2021 Nov 23.

Inner Mongolia Key Laboratory of Environmental Pollution Control & Waste Resource Reuse, School of Ecology and Environment, Inner Mongolia University, Hohhot 010021, China. Electronic address:

Succinate dehydrogenase inhibitor (SDHI) fungicides has been extensively used in agricultural production, which are not easily degrade in the environment and have various toxic effects on aquatic organisms. However, the toxic effects information to non-target organisms were mostly at the racemate level, which were poorly understood at the enantiomers level. Thus, this study aimed to investigate the enantioselective bioaccumulation behavior and toxic effects of penthiopyrad in zebrafish. Read More

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November 2021

Biocatalytic Alkylation Chemistry: Building Molecular Complexity with High Selectivity.

Chempluschem 2021 Nov 8. Epub 2021 Nov 8.

Faculty of Chemistry, Bielefeld University, Universitätsstraße 25, 33615, Bielefeld, Germany.

Biocatalysis has traditionally been viewed as a field that primarily enables access to chiral centers. This includes the synthesis of chiral alcohols, amines and carbonyl compounds, often through functional group interconversion via hydrolytic or oxidation-reduction reactions. This limitation is partly being overcome by the design and evolution of new enzymes. Read More

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November 2021

Kinetic resolution of sulfur-stereogenic sulfoximines by Pd(ii)-MPAA catalyzed C-H arylation and olefination.

Chem Sci 2021 Nov 20;12(44):14863-14870. Epub 2021 Oct 20.

School of Chemistry, University of Hyderabad Hyderabad 500046 India

A direct Pd(ii)-catalyzed kinetic resolution of heteroaryl-enabled sulfoximines through an -C-H alkenylation/arylation of arenes has been developed. The coordination of the sulfoximine pyridyl-motif and the chiral amino acid MPAA ligand to the Pd(ii)-catalyst controls the -discriminating C(aryl)-H activation. This method provides access to a wide range of enantiomerically enriched unreacted aryl-pyridyl-sulfoximine precursors and C(aryl)-H alkenylation/arylation products in good yields with high enantioselectivity (up to >99% ee), and selectivity factor up to >200. Read More

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November 2021

Enantioselective Desymmetrization of 3-Substituted Oxetanes: An Efficient Access to Chiral 3,4-Dihydro-2-1,4-benzoxazines.

Org Lett 2021 Nov 24. Epub 2021 Nov 24.

Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 43 Prague, Czech Republic.

Herein, we describe a versatile transition metal/oxidant free synthesis of the chiral 2-1,4-benzoxazines through chiral phosphoric acid (CPA) catalyzed enantioselective desymmetrization of prochiral oxetanes (30 examples) in up to 99% yield and 99% enantioselectivity under mild reaction conditions. The reported strategy not only complements the conventional 2-1,4-benzoxazine synthetic strategies but also provides access to key intermediates of therapeutic candidates, i.e. Read More

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November 2021

Enantioselective recognition of chiral acids by supramolecular interactions with chiral AIEgens.

Chem Commun (Camb) 2021 Nov 23. Epub 2021 Nov 23.

Shenzhen Institute of Aggregate Science and Technology, School of Science and Engineering, The Chinese University of Hong Kong, Shenzhen, Guangdong 518172, China.

Novel chiral AIEgens bearing optically pure amino groups were synthesized and showed excellent discrimination for a series of chiral acidic compounds and amino acids. Interestingly, after supramolecular assembly with 4-sulfocalix[4]arene, the obtained complexes showed enhanced enantioselectivity for chiral acids. Read More

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November 2021

Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions.

J Am Chem Soc 2021 Nov 23. Epub 2021 Nov 23.

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.

Cooperative asymmetric catalysis with hydrogen chloride (HCl) and chiral dual-hydrogen-bond donors (HBDs) is applied successfully to highly enantioselective Prins cyclization reactions of a wide variety of simple alkenyl aldehydes. The optimal chiral catalysts were designed to withstand the strongly acidic reaction conditions and were found to induce rate accelerations of 2 orders of magnitude over reactions catalyzed by HCl alone. We propose that the combination of strong mineral acids and chiral hydrogen-bond-donor catalysts may represent a general strategy for inducing enantioselectivity in reactions that require highly acidic conditions. Read More

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November 2021

Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents.

Org Lett 2021 Dec 22;23(23):9246-9250. Epub 2021 Nov 22.

School of Chemistry, Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery, Sun Yat-Sen University, Guangzhou 510006, China.

The copper-catalyzed enantioselective C-H arylation between 2-arylindoles and hypervalent iodine reagents has been successfully developed, which provides a convenient and economical route to the highly atroposelective synthesis of axially chiral indole derivatives with a 2-aryl structure (up to 99% ee). Density functional theory calculations and wave function analysis show that the key "sandwich" intermediate leads to high enantioselectivity of the reaction. Read More

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December 2021

Manganese(I)-Catalyzed H-P Bond Activation via Metal-Ligand Cooperation.

J Am Chem Soc 2021 Nov 19. Epub 2021 Nov 19.

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.

Here we report that chiral Mn(I) complexes are capable of H-P bond activation. This activation mode enables a general method for the hydrophosphination of internal and terminal α,β-unsaturated nitriles. Metal-ligand cooperation, a strategy previously not considered for catalytic H-P bond activation, is at the base of the mechanistic action of the Mn(I)-based catalyst. Read More

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November 2021

Designing successful monodentate N-heterocyclic carbene ligands for asymmetric metal catalysis.

Dalton Trans 2021 Nov 17. Epub 2021 Nov 17.

Department of Chemistry, School of Molecular Sciences, University of Western Australia, 35 Stirling Highway, 6009 Crawley, Western Australia, Australia.

Chiral ligands are of particular importance in asymmetric transition-metal catalysis. Although the development of effective chiral monodentate N-heterocyclic carbenes (NHCs) has been slow, a growing amount of papers have been published in recent years showing their unique efficiency as chiral ancillary ligands. Herein we provide an overview of NHC structures that accomplish high levels of enantioselectivity (≥90% ee) and give guidelines to their use and thoughts on the future of this field. Read More

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November 2021

Ir-Catalyzed Enantioselective Formal C-H Conjugate Addition of Pyrrole and Indoles to α,β-Unsaturated Carbonyl Compounds.

Org Lett 2021 Dec 15;23(23):9078-9082. Epub 2021 Nov 15.

Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan.

The chiral Ir(I)-catalyzed intermolecular reaction of -carbamoylpyrrole and indole derivatives with α,β-unsaturated carbonyl compounds such as crotonates proceeded with high enantioselectivity. The obtained chirally functionalized pyrroles and indoles are formal C-H conjugate adducts. The reaction mechanism was studied by deuterium labeling experiments. Read More

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December 2021

Comparison of cyclofructan-, cyclodextrin-, and polysaccharide-based chiral stationary phases for the separation of pharmaceuticals.

Anal Bioanal Chem 2021 Nov 15. Epub 2021 Nov 15.

Department of Chemistry, University of Cyprus, 1678, Nicosia, Cyprus.

In this study, cyclofructan (CF)-, cyclodextrin (CD)-, and polysaccharide-based chiral stationary phases (CSPs) were exploited in high-performance liquid chromatography (HPLC) for the chiral separations of different clinically and pharmaceutically important compounds. In particular, R-naphthylethyl carbamate CF6 (RN-CF6), 3,5-dimethylphenyl carbamate CF7 (DMP-CF7), neutral beta cyclodextrin (β-CD), 3,5-dimethylphenyl carbamate β-CD (DMP-β-CD), and cellulose tris-(3,5-dimethylphenylcarbamate) (Cellulose-Tris DMP) columns were utilized under isocratic elution. The performance of these CSPs as chiral separation media was evaluated by use of nine analytes: acidic, basic, and amphiprotic. Read More

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November 2021

Bi(OAc)/Chiral Phosphoric Acid-Catalyzed Enantioselective 1,2- and Formal 1,4-Allylation Reaction of β,γ-Unsaturated α-Ketoesters.

Org Lett 2021 Dec 15;23(23):9128-9133. Epub 2021 Nov 15.

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.

A highly efficient asymmetric 1,2-allylation reaction of β,γ-unsaturated α-ketoesters was realized by using a Bi(OAc)/chiral phosphoric acid catalyst system under mild conditions. Meanwhile, using this combined strategy of enantioselective 1,2-allylation and subsequent anionic oxy-Cope rearrangement, the asymmetric formal 1,4-allylation reaction was achieved by a one-pot process. These reactions offer rapid access to an array of homoallylic tertiary alcohols and γ-allyl-α-ketoesters with good yields and excellent enantioselectivities. Read More

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December 2021

Characterizing the potentially neuronal acetylcholinesterase reactivity toward chiral pyraclofos: Enantioselective insights from spectroscopy, in silico docking, molecular dynamics simulation and per-residue energy decomposition studies.

J Mol Graph Model 2022 01 1;110:108069. Epub 2021 Nov 1.

School of Water and Environment, Chang'an University, Xi'an, 710054, China; Key Laboratory of Subsurface Hydrology and Ecological Effect in Arid Region of Ministry of Education, Chang'an University, Xi'an, 710054, China; Department of Agricultural Chemistry, Qingdao Agricultural University, Qingdao, 266109, China. Electronic address:

Chiral organophosphorus agents are distributed ubiquitously in the environment, but the neuroactivity of these asymmetric chemicals to humans remains uncertain. This scenario was to explore the stereoselective neurobiological response of human acetylcholinesterase (AChE) to chiral pyraclofos at the enantiomeric scale, and then decipher the microscopic basis of enantioselective neurotoxicity of pyraclofos enantiomers. The results indicated that (R)-/(S)-pyraclofos can form the bioconjugates with AChE with a stoichiometric ratio of 1:1, but the neuronal affinity of (R)-pyraclofos (K = 6. Read More

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January 2022

Synthesis of Novel Crown Ether-Squaramides and Their Application as Phase-Transfer Catalysts.

Molecules 2021 Oct 29;26(21). Epub 2021 Oct 29.

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary.

This work presents the synthesis of six new phase-transfer organocatalysts in which the squaramide unit is directly linked to the nitrogen atom of an aza-crown ether. Four chiral skeletons, namely hydroquinine, quinine, cinchonine (cinchonas), and α-d-glucopyranoside were responsible for the asymmetric construction of an all-carbon quaternary stereogenic center in α-alkylation and Michael addition reactions of malonic esters. We investigated the effects of these different chiral units and that of crown ethers with different sizes on catalytic activity and enantioselectivity. Read More

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October 2021

A Novel Dual Organocatalyst for the Asymmetric Pinder Reaction and a Mechanistic Proposal Consistent with the Isoinversion Effect Thereof.

Molecules 2021 Oct 22;26(21). Epub 2021 Oct 22.

Department of Chemistry, University of Patras, 26504 Patra, Greece.

In general, the Pinder reaction concerns the reaction between an enolisable anhydride and an aldehyde proceeding initially through a Knoevenagel reaction followed by the ring closing process generating lactones with at least two chiral centers. These scaffolds are frequently present in natural products and synthetic bioactive molecules, hence it has attracted intense interest in organic synthesis and medicinal chemistry, particularly with respect to controlling the diastereo- and enantioselectivity. To the best of our knowledge, there has been only one attempt prior to this work towards the development of a catalytic enantioselective Pinder reaction. Read More

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October 2021

Directed Evolution of Artificial Metalloenzymes in Whole Cells.

Angew Chem Int Ed Engl 2021 Nov 11. Epub 2021 Nov 11.

University of California, Department of Chemistry, 718 LATIMER HALL #1460, 94720-1460, Berkeley, UNITED STATES.

Artificial metalloenzymes (ArMs), created by introducing synthetic cofactors into protein scaffolds, are an emerging class of catalyst for non-natural reactions. Read More

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November 2021

Origin of enantioselectivity reversal in Lewis acid-catalysed Michael additions relying on the same chiral source.

Chem Sci 2021 Nov 4;12(42):14133-14142. Epub 2021 Oct 4.

Willard Henry Dow Laboratory, Department of Chemistry, University of Michigan 930 North University Avenue Ann Arbor Michigan 48109 USA

Enantiodivergence is an important concept in asymmetric catalysis that enables access to both enantiomers of a product relying on the same chiral source as reagent. This strategy is particularly appealing as an alternate approach when only one enantiomer of the required chiral ligand is readily accessible but both enantiomers of the product are desired. Despite the potential significance, general catalytic methods to effectively reverse enantioselectivity by changing an achiral reaction parameter remain underdeveloped. Read More

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November 2021

Synthesis and applications of high-performance P-chiral phosphine ligands.

Authors:
Tsuneo Imamoto

Proc Jpn Acad Ser B Phys Biol Sci 2021 ;97(9):520-542

Graduate School of Science, Chiba University.

Metal-catalyzed asymmetric synthesis is one of the most important methods for the economical and environmentally benign production of useful optically active compounds. The success of the asymmetric transformations is significantly dependent on the structure and electronic properties of the chiral ligands coordinating to the center metals, and hence the development of highly efficient ligands, especially chiral phosphine ligands, has long been an important research subject in this field. This review article describes the synthesis and applications of P-chiral phosphine ligands possessing chiral centers at the phosphorus atoms. Read More

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January 2021

Chirally modified cobalt-vanadate grafted on battery waste derived layered reduced graphene oxide for enantioselective photooxidation of 2-naphthol: Asymmetric induction through non-covalent interaction.

J Colloid Interface Sci 2021 Oct 23;608(Pt 2):1526-1542. Epub 2021 Oct 23.

Department of Chemical Sciences, Tezpur University, Assam 784028, India. Electronic address:

The cobalt oxide-vanadium oxide (CoO-VO) combined with reduced graphene oxide (rGO) having band gap of ∼ 3.3 eV appeared as a suitable photocatalyst for selective oxidation of 2-naphthol to BINOL. C2-symmetric BINOL was achieved with good yield using hydrogen peroxide as the oxidant under UV-light irradiation. Read More

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October 2021

Transition metal complexes bearing atropisomeric saturated NHC ligands.

Chirality 2021 Nov 5. Epub 2021 Nov 5.

Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France.

From achiral imidazolinium salts, chiral transition metal complexes containing an N-heterocyclic carbene (NHC) ligand were prepared (metal = palladium, copper, silver, gold, rhodium). Axial chirality in these complexes results from the formation of the metal-carbene bond leading to the restriction of rotation of dissymmetric N-aryl substituents about the C-N bond. When these complexes exhibited a sufficient configurational stability, a resolution by chiral high-performance liquid chromatography (HPLC) on preparative scale enabled isolation of enantiomers with excellent enantiopurities (>99% ee) and good yields. Read More

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November 2021

Macrocylases as synthetic tools for ligand synthesis: enzymatic synthesis of cyclic peptides containing metal-binding amino acids.

R Soc Open Sci 2021 Nov 3;8(11):211098. Epub 2021 Nov 3.

EaStCHEM School of Chemistry, University of Edinburgh, Joseph Black Building, David Brewster Rd, Edinburgh EH9 3FJ, Scotland.

Improving the sustainability of synthesis is a major goal in green chemistry, which has been greatly aided by the development of asymmetric transition metal catalysis. Recent advances in asymmetric catalysis show that the ability to control the coordination sphere of substrates can lead to improvements in enantioselectivity and activity, in a manner resembling the operation of enzymes. Peptides can be used to mimic enzyme structures and their secondary interactions and they are easily accessible through solid-phase peptide synthesis. Read More

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November 2021

Enantioselective Synthesis of Nitriles Containing a Quaternary Carbon Center by Michael Reactions of Silyl Ketene Imines with 1-Acrylpyrazoles.

J Am Chem Soc 2021 Nov 4;143(45):19091-19098. Epub 2021 Nov 4.

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.

The enantioselective construction of quaternary carbon centers is a marked challenge in asymmetric catalysis research. It is extremely difficult when a chiral catalyst can not distinguish the facial selectivity of the substrate through bond interactions. Here we realized an enantioselective Michael reaction of silyl ketene imines to 1-acrylpyrazoles using a chiral -dioxide-Co(II) complex. Read More

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November 2021

Artificial Chiral Interfaces against Amyloid-β Peptide Aggregation: Research Progress and Challenges.

ACS Chem Neurosci 2021 11 1;12(22):4236-4248. Epub 2021 Nov 1.

College of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062, China.

Alzheimer's disease (AD) is a progressive neurodegenerative disorder characterized by an imbalance between the production and clearance of amyloid-β (Aβ) species. AD not only influences the life quality of the patients but also heavily burdens the families and society. Therefore, it is an urgent mission to research and develop some new anti-amyloid aggregation drugs. Read More

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November 2021

Determining the enantioselectivity of asymmetric hydrogenation through parahydrogen-induced hyperpolarization.

J Chem Phys 2021 Oct;155(16):161101

Fujian Provincial Key Laboratory of Plasma and Magnetic Resonance, Department of Electronic Science, Xiamen University, 361005 Xiamen, China.

Asymmetric hydrogenation plays an essential role for both academic research and industry to produce enantiomeric pure chiral molecules. Although nuclear magnetic resonance (NMR) is powerful in determining the yields of hydrogenation, it is still challenging to use NMR for chirality-related analysis. Herein, we applied parahydrogen-induced hyperpolarization (PHIP) NMR to determine the enantioselectivity of asymmetric hydrogenation and the absolute chirality of products. Read More

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October 2021

Copper-catalyzed enantioselective carbonylation toward α-chiral secondary amides.

Chem Sci 2021 Oct 25;12(38):12676-12681. Epub 2021 Aug 25.

Leibniz-Institut für Katalyse e.V. Albert-Einstein-Straße 29a 18059 Rostock Germany

Secondary amides are omnipresent structural motifs in peptides, natural products, pharmaceuticals, and agrochemicals. The copper-catalyzed enantioselective hydroaminocarbonylation of alkenes described in this study provides a direct and practical approach for the construction of α-chiral secondary amides. An electrophilic amine transfer reagent possessing a 4-(dimethylamino)benzoate group was the key to the success. Read More

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October 2021

Pd/GF-Phos-Catalyzed Asymmetric Three-Component Coupling Reaction to Access Chiral Diarylmethyl Alkynes.

J Am Chem Soc 2021 Nov 26;143(43):17983-17988. Epub 2021 Oct 26.

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, People's Republic of China.

Significant attention has been given in the past few years to the selective transformations of -tosylhydrazones to various useful compounds. However, the development of enantioselective versions poses considerable challenges. Herein we report a Pd-catalyzed enantioselective three-component coupling of -tosylhydrazone, aryl halide, and terminal alkyne under mild conditions utilizing a novel chiral sulfinamide phosphine ligand (), which provides a facile access to chiral diarylmethyl alkynes, which are useful synthons in organic synthesis as well as exist as the skeleton in many bioactive molecules. Read More

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November 2021