α-Ketoglutaric acid in Ugi reactions and Ugi/aza-Wittig tandem reactions

• Vladyslav O. Honcharov,
• Yana I. Sakhno,
• Olena H. Shvets,
• Vyacheslav E. Saraev,
• Svitlana V. Shishkina,
• Tetyana V. Shcherbakova and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2021–2029, doi:10.3762/bjoc.21.157

• -methylisoxazol-3-yl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl]acetic acids II (Scheme 1, pathway B). Subsequently, a four-component Ugi reaction of compounds II with temperature-controlled formation of diastereomers of peptidomimetics III was also studied [52]. Taking into account all mentioned above, this work is

• isocyanide (4) in a molar ratio of 1:2:2:2 in MeOH and subsequent stirring at a temperature of 45 °C for 24 hours led to the formation of N1,N5-bis(2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl)-N1,N5-bis(4-chlorophenyl)-2-oxopentanediamide (6a) in 55% yield (Scheme 2, pathway B; Table 2). Compounds 5

• prepare new quinoxalinone derivatives, we studied a tandem combination of Ugi/aza-Wittig reactions involving α-ketoglutaric acid and o-azidoanilines. First, 5-((2-arylazido)(1-aryl-2-(tert-butylamino)-2-oxoethyl)amino)-4,5-dioxopentanoic acids 8a,b,d,f–h were synthesized by the reaction of KGA (1

Understanding the origin of stereoselectivity in the photochemical denitrogenation of 2,3-diazabicyclo[2.2.1]heptene and its derivatives with non-adiabatic molecular dynamics

• Leticia A. Gomes and
• Steven A. Lopez

Beilstein J. Org. Chem. 2025, 21, 2007–2020, doi:10.3762/bjoc.21.156

• isosurface is 0.001. Absorption spectra and geometric overlays corresponding to Wigner-sampled geometries of 1 (a), 3 (b), and 5 (c) with XMS-CASPT2(8,9)/ANO-S-VDZP. Minimum energy path using XMS-CASPT2(8,9)/ANO-S-VDZP for 1 (a), 3 (b), and 5 (c). The dots on the graphs correspond to the S0 (black), S1 (red

• depicted. σCN bonds plotted against each other for 1 (b), 3 (c), and 5 (d). The solid multicolor lines on each plot show the bond lengths over time, and the dots represent the S1/S0 surface hopping points for each trajectory. (a) Geometrical parameters. Plots show trajectories for a 1 ps NAMD simulation

• with CASSCF (8,9)/ANO-S-VDZP, monitoring C–C-bond formation, H–C–C–C dihedral angle, and relative energy for 1 (b), 3 (c), and 5 (d). The energy is relative to the lowest total energy of each trajectory. The red trajectories return to reactant, the green trajectories form retained housane, the blue

Measuring the stereogenic remoteness in non-central chirality: a stereocontrol connectivity index for asymmetric reactions

• Ivan Keng Wee On,
• Yu Kun Choo,
• Sambhav Baid and
• Ye Zhu

Beilstein J. Org. Chem. 2025, 21, 1995–2006, doi:10.3762/bjoc.21.155

• molecule is characterized by the absence of mirror planes and centers of inversion. Central chirality arises when four distinct substituents (a, b, c, and d) are arranged tetrahedrally around a central atom (Scheme 1A). Non-central chirality – such as axial and planar chirality – are becoming increasingly

• can be generated from achiral starting substrates by various means that assemble the four distinct substituents (a, b, c, and d) (Scheme 1D). In the case of central chirality, the differentiating substituents are often directly attached to the newly formed stereocenter. By contrast, for non-central

• chirality, the pairs of substituents (a and b, c and d) are separated in space because the stereogenic scaffolds span multiple atoms. Consequently, bond cleavage and formation occur at positions that are distant from the stereogenic elements and remote from the actual points of differentiation among the

Aryl iodane-induced cascade arylation–1,2-silyl shift–heterocyclization of propargylsilanes under copper catalysis

• Rasma Kroņkalne,
• Rūdolfs Beļaunieks,
• Armands Sebris,
• Anatoly Mishnev and
• Māris Turks

Beilstein J. Org. Chem. 2025, 21, 1984–1994, doi:10.3762/bjoc.21.154

• an internal nucleophile (O-, N-) and reductive elimination affords the arylated product 8 and regenerates the Cu(I) catalyst. The added base (B:) traps the H+, generated in this catalytic cycle. In the case of tert-butyl esters (7: R = COOt-Bu) an equivalent of isobutylene gas is released as a side

• mmol/mL. bNo reaction at 60 and 120 °C. cSame result at 120 °C. Synthesis of lactone and pyrrolidine derivatives. Conditions: ac7e = 0.1 mmol/mL. bReaction conditions modifications: a) 1.2 equiv I-1, CuCl (5 mol %), 60 °C, 3 h, c7f = 0.3 mmol/mL; b) 3.0 equiv I-1, CuCl (10 mol %), 70 °C, 3 h, c7g = 0.1

Photochemical reduction of acylimidazolium salts

• Michael Jakob,
• Nick Bechler,
• Hassan Abdelwahab,
• Fabian Weber,
• Janos Wasternack,
• Leonardo Kleebauer,
• Jan P. Götze and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2025, 21, 1973–1983, doi:10.3762/bjoc.21.153

• suitably electrophilic substrate at the carboxylic acid oxidation level provides an acylazolium species B, which typically reacts directly with nucleophiles or may first be transformed into the corresponding enolate derivative. Regardless of the individual pathway, NHC-catalyzed reactions of this type

• offer many synthetic advantages while the wide availability of chiral NHCs can also allow for high levels of enantioselectivity. As effective enamine and active ester derivatives, Breslow and acylazolium intermediates A and B typically react via classical two-electron polar mechanisms, however, recent

• applications, are underway in our laboratory. (a) Combining N-heterocyclic carbene (NHC) organocatalysis with photoredox catalysis for radical–radical coupling reactions. (b) This work: light-mediated reduction of acylimidazolium species 1 with the tertiary amine DIPEA or the simple silane HSiEt3. Initial test

Asymmetric total synthesis of tricyclic prostaglandin D2 metabolite methyl ester via oxidative radical cyclization

• Miao Xiao,
• Liuyang Pu,
• Qiaoli Shang,
• Lei Zhu and
• Jun Huang

Beilstein J. Org. Chem. 2025, 21, 1964–1972, doi:10.3762/bjoc.21.152

• synthetically challenging because of the tricyclic ring system, spiroketal moiety (B, C-ring), and instability arising from dehydration of the hydroxy groups. Prior approaches to (±)-4 have shown the feasibility of accessing this target molecule. Blair [7] and Sulikowski [8] reported the total synthesis of

Enantioselective desymmetrization strategy of prochiral 1,3-diols in natural product synthesis

• Lihua Wei,
• Rui Yang,
• Zhifeng Shi and
• Zhiqiang Ma

Beilstein J. Org. Chem. 2025, 21, 1932–1963, doi:10.3762/bjoc.21.151

• norlignans hyperione A and ent-hyperione B was reported by the Deska group (Scheme 4) [33]. The synthesis commenced with a two-step conversion of ketone 22 to alkyne 23. Pd-catalyzed Tsuji-type reaction with zinc reagent 24, followed by acetonide hydrolysis, furnished allenic diol 25. Treating allenic diol

• . Alcohol 28 was obtained from 27 in two steps, and was subsequently converted to hyperione A (30) and ent-hyperione B (31) by refluxing in toluene with Shvo’s catalyst 29. Notably, the authors found that hyperione A (30) could be obtained in higher yield and enantiopurity from alcohol 28 via a two-step

• includes two enzymes, CAL-A and CAL-B [35][36]. Although a previous report [27] indicated that the desymmetrization of prochiral diol 2 with CAL was ineffective, the Shishido group prepared optically active compound (S)-11 via CAL-catalyzed asymmetric transesterification of the structurally similar diol 10

Rhodium-catalysed connective synthesis of diverse reactive probes bearing S(VI) electrophilic warheads

• Scott Rice,
• Julian Chesti,
• William R. T. Mosedale,
• Megan H. Wright,
• Stephen P. Marsden,
• Terry K. Smith and
• Adam Nelson

Beilstein J. Org. Chem. 2025, 21, 1924–1931, doi:10.3762/bjoc.21.150

• estimation of the yield of each product (Figure 2, panel B). It was found that many reactions involving alcohol- (e.g., C1–5, C8, C11 and C14) and indole- (e.g., C3, C12 and C15) containing co-substrates yielded intermolecular products, whilst those involving nitrile-containing co-substrates (C9 and 10) and

• subsequently used. Panel B: yields, estimated by evaporative light scattering detection, of reactions involving combinations of substrates, co-substrates and catalysts (dash: <2% estimated yield). Highlighted combinations (green boxes) were selected for mass-directed purification. aMultiple intermolecular

• substrates D1–5 of general structure 2 bearing S(VI) electrophiles. Panel A: Overview of synthesis (see Table 1 for details of synthesis of individual substrates). Panel B: Substrates that were prepared. Synthesis of α-diazoamide substrates of general structure 2 bearing S(VI) electrophiles (see Scheme 1

Synthesis of N-doped chiral macrocycles by regioselective palladium-catalyzed arylation

• Shuhai Qiu and
• Junzhi Liu

Beilstein J. Org. Chem. 2025, 21, 1917–1923, doi:10.3762/bjoc.21.149

• bromide (see Supporting Information File 1). Subsequent Buchwald–Hartwig reaction with 1,3-dibromo-7-tert-butylpyrene (2) gave the [2 + 2] macrocyclic precursors 3a,b as the major product in 16%/10% yields, and trace amounts of higher oligomers as detected by mass spectrometry. Notably, compounds 3a,b

• % and 90%, respectively. For MC2, four C–C bonds are formed between the dichlorobenzene units and tert-butylphenyl groups, generating two dihydroindolo[2,3-b]carbazole subunits. In contrast, there is only one newly formed C–C bond between the dichlorobenzene unit and one pyrene moiety for MC1

• planar dihydroindolo[2,3-b]carbazole subunits orienting upwards with a dihedral angle of 75° and two pyrene units downwards (Figure 2b). Besides, the central cavity is highly symmetric, and the shortest diameters are determined to be 4.34 Å and 4.99 Å, respectively. In contrast to MC2, MC3 shows an

Synthesis, biological and electrochemical evaluation of glycidyl esters of phosphorus acids as potential anticancer drugs

• Almaz A. Zagidullin,
• Emil R. Bulatov,
• Mikhail N. Khrizanforov,
• Damir R. Davletshin,
• Elvina M. Gilyazova,
• Ivan A. Strelkov and
• Vasily A. Miluykov

Beilstein J. Org. Chem. 2025, 21, 1909–1916, doi:10.3762/bjoc.21.148

• or aziridine fragments. Dose–response curves for the cytotoxic effects of glycidyl esters of phosphorus acids 1–3 on human cell lines. (A) Human skin fibroblasts (HSF), (B) prostate cancer cells (PC-3), and (C) breast cancer cells (MCF7) were treated with diglycidyl methylphosphonate (1, red

Chiral phosphoric acid-catalyzed asymmetric synthesis of helically chiral, planarly chiral and inherently chiral molecules

• Wei Liu and
• Xiaoyu Yang

Beilstein J. Org. Chem. 2025, 21, 1864–1889, doi:10.3762/bjoc.21.145

• interactions with the enehydrazine intermediate, which is essential for achieving high levels of stereocontrol. Using the optimal catalyst CPA 1, a series of aza[6]helicenes 3a,b was synthesized with excellent enantioselectivity and high yield. However, this method demonstrated notably reduced efficiency and

• demonstrated the successful construction of planarly chiral macrocycles with 12- to 14-membered ansa chains with high enantioselectivity when using NH2 as the directing group (see 33a,b). However, extending the ansa chain to 15 members led to the loss of planar chirality due to insufficient steric hindrance to

• for the asymmetric synthesis of saddle-shaped inherently chiral dibenzo[b,f][1,5]diazocines 72 via CPA catalysis [55]. In the presence of CPA 7 (10 mol %) and the corresponding 2-acylaniline 73 (20 mol %) as co-catalysts, the asymmetric dimerization of 2-acylbenzo isocyanates 71 allowed access to

Systematic pore lipophilization to enhance the efficiency of an amine-based MOF catalyst in the solvent-free Knoevenagel reaction

• Pricilla Matseketsa,
• Margret Kumbirayi Ruwimbo Pagare and
• Tendai Gadzikwa

Beilstein J. Org. Chem. 2025, 21, 1854–1863, doi:10.3762/bjoc.21.144

• catalysis via the rational functionalization of MOF pores. Schematic representation of the modulation of MOF pore environments. A) de novo synthesis of several MOFs requiring the multistep synthesis of different organic linkers. B) Synthesis of several frameworks from a single parent MOF using post

• -synthesis modification (PSM). A) Schematic representation of the reaction of KSU-1 with aliphatic isocyanates and the estimated conversions at –OH and –NH2. B) The corresponding 1H NMR spectra of the MOF reaction products digested in a solution of D2SO4 in DMSO-d6. A) Schematic representation of the

• reaction between benzaldehyde and malononitrile to form benzylidenemalononitrile (BMN). B) Representative 1H NMR spectra for the reaction of benzaldehyde and malononitrile in toluene with dodecane as internal standard, analyzed after 30 minutes. Graphical representation of the Knoevenagel catalysis results

Photoswitches beyond azobenzene: a beginner’s guide

• Michela Marcon,
• Christoph Haag and
• Burkhard König

Beilstein J. Org. Chem. 2025, 21, 1808–1853, doi:10.3762/bjoc.21.143

• forward and backward isomerisation can occur simultaneously. Moreover, some unwanted photochemical side reactions ΦS can occur, as shown in the Equation 4: A is one state of the photoswitch, B the second state, and B’ a generic degradation product. Fatigue resistance measures how many times the

• be synthesised through oxidation of aminoheteroarenes 12 (Scheme 4A) or reduction of nitroheteroarenes 13 (B). Bayer–Mills coupling (Scheme 4C) is suitable for both symmetric and asymmetric targets, usually in acidic conditions. Basic conditions [14] are more effective with very electron-poor

• aromatic amines. Another strategy for both symmetric and asymmetric targets is the azo coupling of a diazonium salt 15 (Scheme 5A) with a nucleophile, which can be a (hetero)aromatic 16 [29] (B), a lithiated ring 19 [39] (C), or a precursor 20a,b [29][32][40] (D). In case of more than one reactive position

[3 + 2] Cycloaddition of thioformylium methylide with various arylidene-azolones in the synthesis of 7-thia-3-azaspiro[4.4]nonan-4-ones

• Daniil I. Rudik,
• Irina V. Tiushina,
• Anatoly I. Sokolov,
• Alexander Yu. Smirnov,
• Alexander R. Romanenko,
• Alexander A. Korlyukov,
• Andrey A. Mikhaylov and
• Mikhail S. Baranov

Beilstein J. Org. Chem. 2025, 21, 1791–1798, doi:10.3762/bjoc.21.141

• product. Next, using the revealed optimal reaction conditions, we studied its scope on a variety of arylidene-azolones 1–4 (Scheme 3). We also tried to apply both proposed approaches (methods A and B) to the series of derivatives 5. In contrast to the results obtained previously for N-benzylazomethine

• would be of help in further drug design of spirocyclic scaffolds. Single crystal X-ray analysis for the compounds 6e (A), 7d (B), 8e (C) and 9e (D). Atoms are shown as thermal ellipsoids at 50% probability. All hydrogen atoms, except the one at the stereogenic center, are omitted for clarity. Synthetic

Synthesis of chiral cyclohexane-linked bisimidazolines

• Changmeng Xi,
• Qingshan Sun and
• Jiaxi Xu

Beilstein J. Org. Chem. 2025, 21, 1786–1790, doi:10.3762/bjoc.21.140

• nucleophilically attacks the phosphonium in A to generate intermediate B by loss of triphenylphosphine oxide and triflic acid. The nucleophilic sulfonamide in B intramolecularily attacks the generated imine moiety in B to form intermediate C, in which triflic acid may protonate the imine moiety in B to assist the

Research progress on calixarene/pillararene-based controlled drug release systems

• Liu-Huan Yi,
• Jian Qin,
• Si-Ran Lu,
• Liu-Pan Yang,
• Li-Li Wang and
• Huan Yao

Beilstein J. Org. Chem. 2025, 21, 1757–1785, doi:10.3762/bjoc.21.139

Unique halogen–π association detected in single crystals of C–N atropisomeric N-(2-halophenyl)quinolin-2-one derivatives and the thione analogue

• Mai Uchibori,
• Nanami Murate,
• Kanako Shima,
• Tatsunori Sakagami,
• Ko Kanehisa,
• Gary James Richards,
• Akiko Hori and
• Osamu Kitagawa

Beilstein J. Org. Chem. 2025, 21, 1748–1756, doi:10.3762/bjoc.21.138

• halogen bonding observed in C–N atropisomeric quinazolinone I and quinazoline-thione II. Although the catalytic asymmetric synthesis of N-(2-bromo- or 2-chloro-phenyl)quinolin-2-ones 1a,b was recently attempted by Doerfler et al., the yields were moderate (33% and 48%) and the enantioselectivities were

• poor (11% ee and 9% ee) [31]. In addition, rotational stability about the C–N bond in 1a,b was not mentioned at all. We prepared racemates rac-1a,b in accordance with Scheme 1 and separated their enantiomers [(P)-1a,b and (M)-1a,b] through medium pressure liquid chromatography (MPLC) using a semi

• -preparative chiral IH column. The rotational barriers of 1a and 1b were evaluated to be 32.0 and 30.8 kcal mol−1, respectively, by a thermal racemization experiment of the separated (P)-1a and (P)-1b. In contrast to quinolinones 1a,b, the atropisomers in the precursors (3,4-dihydroquinolinones 4a,b) could not

Thermodynamics and polarity-driven properties of fluorinated cyclopropanes

• Matheus P. Freitas

Beilstein J. Org. Chem. 2025, 21, 1742–1747, doi:10.3762/bjoc.21.137

• molecules (QTAIM) analyses were carried out with the AIMAll program [27]. Structures of fluorinated cyclopropanes evaluated in this study through quantum chemical methods. (a) Electrostatic potential map of 1.2.3-c.c., highlighting the negative region (top side) and positive region (bottom side). (b) Top

Preparation of a furfural-derived enantioenriched vinyloxazoline building block and exploring its reactivity

• Madara Darzina,
• Anna Lielpetere and
• Aigars Jirgensons

Beilstein J. Org. Chem. 2025, 21, 1737–1741, doi:10.3762/bjoc.21.136

• -wise process [22]. The first step involves addition of the oxazoline nitrogen to TsNCO leading to a zwitterionic intermediate A, which undergoes 1,4-conjugate addition forming a cyclic intermediate B. Subsequently, the electron-rich double bond in intermediate B reacts with a second equivalent of TsNCO

Convenient alternative synthesis of the Malassezia-derived virulence factor malassezione and related compounds

• Karu Ramesh and
• Stephen L. Bearne

Beilstein J. Org. Chem. 2025, 21, 1730–1736, doi:10.3762/bjoc.21.135

• neurological disorders [7] and possibly other non-skin diseases [5]. These fungi, especially M. furfur, convert tryptophan into various alkaloid indoles such as malassezione (1), malassezin (2), which cyclizes to indolo[3,2-b]carbazole (3), other related indolo[3,2-b]carbazoles (4–7), pityriarubins (8–10), and

• the presence of the indole groups. General procedure for the synthesis of ketones 25a,b, and d from acids 24a,b, and d. Adapting DCC/DMAP protocols reported previously [22][23][24][25][26][27], an oven-dried 50 mL flask equipped with a magnetic stir bar was charged with the acid (1 equiv, typically

• ] or B) indole-3-acetic acid. Various bis-substituted ketones prepared. a25c prepared from 25b. Supporting Information Supporting Information File 6: Copies of NMR and MS spectra of synthesized compounds. Funding This work was supported by a Discovery Grant from the Natural Sciences and Engineering

3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units

• Somayyeh Kheirjou,
• Jan Riebe,
• Maike Thiele,
• Christoph Wölper and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2025, 21, 1719–1729, doi:10.3762/bjoc.21.134

• that we reacted either (S)- or (R)-H-2 with the dichloride (S)-iPr-62 to give the diastereomeric macrocycles (S,S)-HiPr-M22 and (R,S)-HiPr-M22 in 73/49% yield, respectively. The 1H NMR spectra of the C2-symmetric derivatives (S,S)-H/iPr-M22 (see Figure 8a/b) differ most significantly in the splitting

• routes towards macrocycles featuring one BINOL unit. a) Two-fold Suzuki coupling and b) two-fold Williamson synthesis. Reagents and conditions: i) bis(boronic ester) 75/6/7/8 (1.0. equiv), Pd2(dba)3 (0.1 equiv), P(o-Tol)3 (0.2 equiv), n-Bu4N+OH− (3.2. equiv), toluene/H2O 5:1, 90 °C; ii) ethylene glycol

• -62; ii) Me/(S)-H/(R)-H/iPr-2 (1.0 equiv), Cs2CO3 (3.2 equiv), CH3CN, 80 °C. 1H NMR spectra of a) (S,S)-H-M22, b) (S,S)-iPr-M22, c) (S,S)-HiPr-M22, and d) (R,S)-HiPr-M22 (all: 400 MHz, CDCl3, 298 K, for labelling see Figure 7). Supporting Information Synthetic procedures and NMR spectra for all new

Continuous-flow-enabled intensification in nitration processes: a review of technological developments and practical applications over the past decade

• Feng Zhou,
• Chuansong Duanmu,
• Yanxing Li,
• Jin Li,
• Haiqing Xu,
• Pan Wang and
• Kai Zhu

Beilstein J. Org. Chem. 2025, 21, 1678–1699, doi:10.3762/bjoc.21.132

• nitric acid and the model was formulated to predict the reaction outcome at large capacity. Lan and Lu [32] developed a method for the rapid determination of lumped kinetics for the nitration of o-dichlorobenzene by processing the profile of adiabatic temperature rise in a micropacked-bed reactor. Type B

Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides

• Tsun-Yi Chiang,
• Mei-Huei Lin,
• Chun-Wei Chang,
• Jinq-Chyi Lee and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2025, 21, 1671–1677, doi:10.3762/bjoc.21.131

• a = 16.1017(4) Å, b = 7.7608(2) Å, c = 28.8344(8) Å, and β = 93.3680(10)°. Additionally, the presence of lattice water greatly influenced the molecular packing. The hydrogen bond (H–O–H) lengths in this lattice water ranged from 1.923 to 2.204 Å (Figure 2b). The pyruvylated galactose 6 was utilized

• ), 1.15 EPS (2) and Rhizobium leguminosarum bv. viciae VF39 EPS (3). (a) Oak Ridge Thermal Ellipsoid Plot view of the X-ray crystal structure of pyruvylated galactose 6. (b) Hydrogen-bonding in the crystal structure of pyruvylated galactose 6. Synthesis of trisaccharide precursor 14. Optimization of

Influence of the cation in hypophosphite-mediated catalyst-free reductive amination

• Natalia Lebedeva,
• Fedor Kliuev,
• Olesya Zvereva,
• Klim Biriukov,
• Evgeniya Podyacheva,
• Maria Godovikova,
• Oleg I. Afanasyev and
• Denis Chusov

Beilstein J. Org. Chem. 2025, 21, 1661–1670, doi:10.3762/bjoc.21.130

• dimethylamine and benzaldehyde promoted by hypophosphorous acid. Rationale of the current study: a) Our previous work [20]; b) this work. Comparison of KH2PO2 and NaH2PO2 under the optimal conditions. Control experiments. Experiments with D3PO2. Principal steps of the mechanism of the reductive amination with

Catalytic asymmetric reactions of isocyanides for constructing non-central chirality

• Jia-Yu Liao

Beilstein J. Org. Chem. 2025, 21, 1648–1660, doi:10.3762/bjoc.21.129

• condensation between 27 and the aldehyde afforded INT-A, which was activated by the CPA catalyst through hydrogen bonding interaction. The nucleophilic addition of isocyanide to Int-A produced INT-B bearing a stereogenic center. Subsequently, INT-B underwent intramolecular cyclization to generate axially

• non-central chiral compounds. a) Common types of chirality. b) Representative functional molecules bearing non-central chirality. Construction of planar chirality. Construction of axial chirality. Construction of inherent chirality. Construction of helical chirality. CPA-catalyzed enantioselective