{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:43:26Z","timestamp":1760143406383,"version":"build-2065373602"},"reference-count":61,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2024,1,18]],"date-time":"2024-01-18T00:00:00Z","timestamp":1705536000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"MIUR","award":["2017YXX8AZ","POR FESR 2014-2020-Call HUB Ricerca e Innovazione, Progetto 1139857 CE4WE"],"award-info":[{"award-number":["2017YXX8AZ","POR FESR 2014-2020-Call HUB Ricerca e Innovazione, Progetto 1139857 CE4WE"]}]},{"name":"Regione Lombardia","award":["2017YXX8AZ","POR FESR 2014-2020-Call HUB Ricerca e Innovazione, Progetto 1139857 CE4WE"],"award-info":[{"award-number":["2017YXX8AZ","POR FESR 2014-2020-Call HUB Ricerca e Innovazione, Progetto 1139857 CE4WE"]}]},{"name":"Shimadzu UHPLC","award":["2017YXX8AZ","POR FESR 2014-2020-Call HUB Ricerca e Innovazione, Progetto 1139857 CE4WE"],"award-info":[{"award-number":["2017YXX8AZ","POR FESR 2014-2020-Call HUB Ricerca e Innovazione, Progetto 1139857 CE4WE"]}]},{"name":"Ministero dell\u2019Universit\u00e0 e della Ricerca (MUR)","award":["2017YXX8AZ","POR FESR 2014-2020-Call HUB Ricerca e Innovazione, Progetto 1139857 CE4WE"],"award-info":[{"award-number":["2017YXX8AZ","POR FESR 2014-2020-Call HUB Ricerca e Innovazione, Progetto 1139857 CE4WE"]}]},{"name":"University of Pavia","award":["2017YXX8AZ","POR FESR 2014-2020-Call HUB Ricerca e Innovazione, Progetto 1139857 CE4WE"],"award-info":[{"award-number":["2017YXX8AZ","POR FESR 2014-2020-Call HUB Ricerca e Innovazione, Progetto 1139857 CE4WE"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>Triptycenes are tridimensional molecular scaffolds with interesting properties for applications in materials science: molecular rigidity and preorganization, tailorable chromophores, and, with an appropriate substitution pattern, chirality. The separation of the two enantiomers of chiral triptycenes has been the subject of increasing interest in recent years, with limited success. Here, we report the synthesis and characterization of a series of new organic compounds, in which a chiral triptycene scaffold, derivatized in the 2 and 6 positions with amino groups, has been functionalized with different enantiopure chiral auxiliaries, forming diastereoisomeric couples. The properties of such compounds, in terms of the optimization of their chromatographic separation, are elucidated with the aid of computational calculations of preferred conformations and molecular polarities.<\/jats:p>","DOI":"10.3390\/sym16010116","type":"journal-article","created":{"date-parts":[[2024,1,18]],"date-time":"2024-01-18T11:28:46Z","timestamp":1705577326000},"page":"116","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis of 2,6-Diaminotriptycene Conjugates with Chiral Auxiliaries: Towards the Scalable Resolution of Crucial Triptycene Intermediates"],"prefix":"10.3390","volume":"16","author":[{"ORCID":"https:\/\/orcid.org\/0009-0003-4818-7548","authenticated-orcid":false,"given":"Giovanni","family":"Preda","sequence":"first","affiliation":[{"name":"Department of Chemistry and INSTM, University of Pavia, Via Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7501-5213","authenticated-orcid":false,"given":"Emanuele","family":"Casali","sequence":"additional","affiliation":[{"name":"Department of Chemistry and INSTM, University of Pavia, Via Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alessio","family":"Porta","sequence":"additional","affiliation":[{"name":"Department of Chemistry and INSTM, University of Pavia, Via Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8273-3798","authenticated-orcid":false,"given":"Dario","family":"Pasini","sequence":"additional","affiliation":[{"name":"Department of Chemistry and INSTM, University of Pavia, Via Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,1,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1038\/440163a","article-title":"Nanomotor Rotates Microscale Objects","volume":"440","author":"Eelkema","year":"2006","journal-title":"Nature"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"7165","DOI":"10.1039\/C4NR00801D","article-title":"Nanostructuring with Chirality: Binaphthyl-Based Synthons for the Production of Functional Oriented Nanomaterials","volume":"6","author":"Caricato","year":"2014","journal-title":"Nanoscale"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"11331","DOI":"10.1038\/ncomms11331","article-title":"Dispersion and Shape Engineered Plasmonic Nanosensors","volume":"7","author":"Jeong","year":"2016","journal-title":"Nat. Commun."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"461","DOI":"10.1038\/nmat4525","article-title":"Reconfigurable Chiroptical Nanocomposites with Chirality Transfer from the Macro- to the Nanoscale","volume":"15","author":"Kim","year":"2016","journal-title":"Nat. Mater."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1021\/cr050005k","article-title":"Chirality-Sensing Supramolecular Systems","volume":"108","author":"Hembury","year":"2008","journal-title":"Chem. Rev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1038\/s41586-022-05305-9","article-title":"A Tape-Reading Molecular Ratchet","volume":"612","author":"Ren","year":"2022","journal-title":"Nature"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1908021","DOI":"10.1002\/adma.201908021","article-title":"Aggregation-Induced Circularly Polarized Luminescence: Chiral Organic Materials for Emerging Optical Technologies","volume":"32","author":"Nitti","year":"2020","journal-title":"Adv. Mater."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"857","DOI":"10.1021\/cr040079g","article-title":"BINOL:\u2009 A Versatile Chiral Reagent","volume":"105","author":"Brunel","year":"2005","journal-title":"Chem. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"9009","DOI":"10.1021\/jacs.1c05172","article-title":"Sterics and Hydrogen Bonding Control Stereochemistry and Self-Sorting in BINOL-Based Assemblies","volume":"143","author":"Zou","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"e202315990","DOI":"10.1002\/anie.202315990","article-title":"A Chiral Emissive Conjugated Corral for High-Affinity and Highly Enantioselective Recognition in Water","volume":"62","author":"Fu","year":"2023","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1181","DOI":"10.1021\/ar800107v","article-title":"Iptycenes in the Design of High Performance Polymers","volume":"41","author":"Swager","year":"2008","journal-title":"Acc. Chem. Res."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Wo\u017any, M., Mames, A., and Ratajczyk, T. (2022). Triptycene Derivatives: From Their Synthesis to Their Unique Properties. Molecules, 27.","DOI":"10.3390\/molecules27010250"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"10047","DOI":"10.1039\/D1OB01818C","article-title":"Recent Advances on Triptycene Derivatives in Supramolecular and Materials Chemistry","volume":"19","author":"Gu","year":"2021","journal-title":"Org. Biomol. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2093","DOI":"10.1021\/acs.accounts.8b00268","article-title":"Triptycene-Derived Macrocyclic Arenes: From Calixarenes to Helicarenes","volume":"51","author":"Chen","year":"2018","journal-title":"Acc. Chem. Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"3301","DOI":"10.1039\/b900754g","article-title":"Iptycenes in Supramolecular and Materials Chemistry","volume":"38","author":"Chong","year":"2009","journal-title":"Chem. Soc. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1002\/open.202000077","article-title":"Chiral Triptycenes in Supramolecular and Materials Chemistry","volume":"9","author":"Preda","year":"2020","journal-title":"ChemistryOpen"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"7059","DOI":"10.1002\/chem.202005317","article-title":"Chiral Triptycenes: Concepts, Progress and Prospects","volume":"27","author":"Khan","year":"2021","journal-title":"Chem. A Eur. J."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2301857","DOI":"10.1002\/adom.202301857","article-title":"Chain-Length Dependence of the Optical Activity of Helical Triptycene-Based \u03c0-Conjugated Ladder Polymers","volume":"12","author":"Lupton","year":"2024","journal-title":"Adv. Opt. Mater."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4696","DOI":"10.1021\/jacs.8b13865","article-title":"Triptycene-Based Ladder Polymers with One-Handed Helical Geometry","volume":"141","author":"Ikai","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"8989","DOI":"10.1039\/D3CC02259E","article-title":"Optically-Pure Triptycene-Based Metallomacrocycles and Homochiral Self-Sorting Assisted by Ladder Formation","volume":"59","author":"Oki","year":"2023","journal-title":"Chem. Commun."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"364","DOI":"10.1021\/acsmacrolett.8b00106","article-title":"Circularly Polarized Luminescent Triptycene-Based Polymers","volume":"7","author":"Ikai","year":"2018","journal-title":"ACS Macro Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"8440","DOI":"10.1039\/C7OB02046E","article-title":"Chiral Triptycene-Pyrene \u03c0-Conjugated Chromophores with Circularly Polarized Luminescence","volume":"15","author":"Ikai","year":"2017","journal-title":"Org. Biomol. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1021\/acs.organomet.1c00447","article-title":"Synthesis, Characterization, and Photophysical Properties of Triptycene-Based Chiral Organoboranes","volume":"41","author":"Zhang","year":"2022","journal-title":"Organometallics"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"e202202527","DOI":"10.1002\/anie.202202527","article-title":"Enantiomeric Water-Soluble Octopus[3]Arenes for Highly Enantioselective Recognition of Chiral Ammonium Salts in Water","volume":"61","author":"Han","year":"2022","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3646","DOI":"10.1246\/bcsj.45.3646","article-title":"Optically Active Triptycenes. II. Synthesis of Optically Active 7-Substituted 2,5-Dimethoxytriptycenes","volume":"45","author":"Ogura","year":"1972","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1246\/bcsj.38.155","article-title":"The Optical Rotatory Dispersion of Triptycene Derivatives. The Direction of Electronic Polarization as a Determining Factor of the Sign of the RD Curve","volume":"38","author":"Ogura","year":"1965","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"853","DOI":"10.1246\/bcsj.35.853","article-title":"Synthesis of Trisubstituted Triptycenes and the Optical Resolution of 7-Carboxy-2,5-Diacetoxytriptycene","volume":"35","author":"Sonoda","year":"1962","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"10171","DOI":"10.1021\/acs.joc.3c01197","article-title":"Shape-Persistent Triptycene-Derived Pillar[6]Arenes: Synthesis, Host\u2013Guest Complexation, and Enantioselective Recognitions of Chiral Ammonium Salts","volume":"88","author":"Liu","year":"2023","journal-title":"J. Org. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/j.tetasy.2014.11.012","article-title":"Asymmetric Synthesis of Multi-Substituted Triptycenes via Enantioselective Alkynylation of 1,5-Dibromoanthracene-9,10-Dione","volume":"26","author":"Shibata","year":"2015","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3004","DOI":"10.1002\/chem.201905519","article-title":"Enantioselective Synthesis of Distorted \u03c0-Extended Chiral Triptycenes Consisting of Three Distinct Aromatic Rings by Rhodium-Catalyzed [2+2+2] Cycloaddition Available","volume":"26","author":"Aida","year":"2020","journal-title":"Chem. Eur. J."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"106355","DOI":"10.1016\/j.orgel.2021.106355","article-title":"Triptycene-Derived TADF Enantiomers Displaying Circularly Polarized Luminescence and High-Efficiency Electroluminescence","volume":"99","author":"Wang","year":"2021","journal-title":"Org. Electron."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2106418","DOI":"10.1002\/adfm.202106418","article-title":"High-Performance Solution-Processed Nondoped Circularly Polarized OLEDs with Chiral Triptycene Scaffold-Based TADF Emitters Realizing Over 20% External Quantum Efficiency","volume":"31","author":"Wang","year":"2021","journal-title":"Adv. Funct. Mater."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"12781","DOI":"10.1002\/anie.202102350","article-title":"Triptycene-Based Chiral Porous Polyimides for Enantioselective Membrane Separation","volume":"60","author":"Zhang","year":"2021","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"5304","DOI":"10.1002\/anie.201600911","article-title":"Triptycene-Based Chiral Macrocyclic Hosts for Highly Enantioselective Recognition of Chiral Guests Containing a Trimethylamino Group","volume":"55","author":"Zhang","year":"2016","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"16036","DOI":"10.1002\/chem.202002781","article-title":"A Triptycene-Based Enantiopure Bis(Diazadibenzoanthracene) by a Chirality-Assisted Synthesis Approach","volume":"26","author":"Wang","year":"2020","journal-title":"Chem. Eur. J."},{"key":"ref_36","first-page":"6","article-title":"Synthesis of Substituted Iptycenes","volume":"26","author":"Ma","year":"2015","journal-title":"Syn. Lett."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"658","DOI":"10.1246\/cl.2010.658","article-title":"Triptycene Derivatives: Synthesis and Applications","volume":"39","author":"Zhao","year":"2010","journal-title":"Chem. Lett."},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Chen, C.-F., and Ma, Y.-X. (2013). Iptycenes Chemistry: From Synthesis to Applications, Springer.","DOI":"10.1007\/978-3-642-32888-6"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"883","DOI":"10.1002\/chir.23358","article-title":"Triptycene Derivatives as Chiral Probes for Studying the Molecular Enantiorecognition on Sub-2-\u039cm Particle Cellulose Tris(3,5-Dimethylphenylcarbamate) Chiral Stationary Phase","volume":"33","author":"Rosetti","year":"2021","journal-title":"Chirality"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Rizzo, S., Benincori, T., Fontana, F., Pasini, D., and Cirilli, R. (2022). HPLC Enantioseparation of Rigid Chiral Probes with Central, Axial, Helical, and Planar Stereogenicity on an Amylose (3,5-Dimethylphenylcarbamate) Chiral Stationary Phase. Molecules, 27.","DOI":"10.3390\/molecules27238527"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"6490","DOI":"10.1021\/acs.orglett.3c02093","article-title":"Activation of Solid-State Emission and Photostability through Molecular Confinement: The Case of Triptycene-Fused Quinacridone Dyes","volume":"25","author":"Preda","year":"2023","journal-title":"Org. Lett."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"5882","DOI":"10.1021\/acs.orglett.5b03066","article-title":"Synthesis, Structure, and Complexation Properties of a C3-Symmetrical Triptycene-Based Anion Receptor: Selectivity for Dihydrogen Phosphate","volume":"17","author":"Granda","year":"2015","journal-title":"Org. Lett."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"6880","DOI":"10.1021\/ma8012527","article-title":"Synthesis and Characterization of Poly(2,6-Triptycene)","volume":"41","author":"Chen","year":"2008","journal-title":"Macromolecules"},{"key":"ref_44","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2019). Gaussian16, Revision, C.01, Gaussian, Inc."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","article-title":"Density-Functional Thermochemistry. III. The Role of Exact Exchange","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"724","DOI":"10.1063\/1.1674902","article-title":"Self-Consistent Molecular-Orbital Methods. IX. An Extended Gaussian-Type Basis for Molecular-Orbital Studies of Organic Molecules","volume":"54","author":"Ditchfield","year":"1971","journal-title":"J. Chem. Phys."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1007\/BF00533485","article-title":"The Influence of Polarization Functions on Molecular Orbital Hydrogenation Energies","volume":"28","author":"Hariharan","year":"1973","journal-title":"Theor. Chim. Acta"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.1063\/1.1677527","article-title":"Self\u2014Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian\u2014Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules","volume":"56","author":"Hehre","year":"1972","journal-title":"J. Chem. Phys."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1007\/s00214-007-0310-x","article-title":"The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals","volume":"120","author":"Zhao","year":"2008","journal-title":"Theor. Chem. Acc."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"3297","DOI":"10.1039\/b508541a","article-title":"Balanced Basis Sets of Split Valence, Triple Zeta Valence and Quadruple Zeta Valence Quality for H to Rn: Design and Assessment of Accuracy","volume":"7","author":"Weigend","year":"2005","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1057","DOI":"10.1039\/b515623h","article-title":"Accurate Coulomb-Fitting Basis Sets for H to Rn","volume":"8","author":"Weigend","year":"2006","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"6378","DOI":"10.1021\/jp810292n","article-title":"Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions","volume":"113","author":"Marenich","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"6478","DOI":"10.1021\/acs.joc.0c00396","article-title":"Chiral Derivatives of 2-Aminotribenzotriquinacene: Synthesis and Optical Resolution","volume":"85","author":"Li","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"4891","DOI":"10.1021\/acs.joc.7b00711","article-title":"Triflic Acid Promoted Decarboxylation of Adamantane-Oxazolidine-2-One: Access to Chiral Amines and Heterocycles","volume":"82","author":"Hrdina","year":"2017","journal-title":"J. Org. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"6169","DOI":"10.1016\/j.tet.2012.05.073","article-title":"Chemical Resolution of Enantiomers of 3,4-Dihydropyrimidin-2(1H)-Ones Using Chiral Auxiliary Approach","volume":"68","author":"Singh","year":"2012","journal-title":"Tetrahedron"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"2349","DOI":"10.1002\/(SICI)1521-3773(19980918)37:17<2349::AID-ANIE2349>3.0.CO;2-I","article-title":"The Family Approach to the Resolution of Racemates","volume":"37","author":"Vries","year":"1998","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"4206","DOI":"10.1016\/j.tet.2010.03.102","article-title":"Shape Selectivity in the Synthesis of Chiral Macrocyclic Amides","volume":"66","author":"Colombo","year":"2010","journal-title":"Tetrahedron"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1807","DOI":"10.1039\/b924400j","article-title":"Locked Chromophores as CD and NMR Probes for the Helical Conformation of Tetraamidic Macrocycles","volume":"8","author":"Coluccini","year":"2010","journal-title":"Org. Biomol. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"776","DOI":"10.1002\/chir.23103","article-title":"Use of chiral auxiliaries in the asymmetric synthesis of biologically active compounds: A review","volume":"31","author":"Miranda","year":"2019","journal-title":"Chirality"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"5385","DOI":"10.1016\/j.tet.2015.05.105","article-title":"Stereoselective and regioselective one-pot synthesis of polyhydroxy bicyclic diazenes and hydrazones from methyl 6-deoxy-6-iodo-hexosides","volume":"71","author":"Li","year":"2015","journal-title":"Tetrahedron"}],"container-title":["Symmetry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-8994\/16\/1\/116\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T13:49:56Z","timestamp":1760104196000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-8994\/16\/1\/116"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,1,18]]},"references-count":61,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2024,1]]}},"alternative-id":["sym16010116"],"URL":"https:\/\/doi.org\/10.3390\/sym16010116","relation":{},"ISSN":["2073-8994"],"issn-type":[{"type":"electronic","value":"2073-8994"}],"subject":[],"published":{"date-parts":[[2024,1,18]]}}}