{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T01:04:33Z","timestamp":1760231073292,"version":"build-2065373602"},"reference-count":61,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2022,8,27]],"date-time":"2022-08-27T00:00:00Z","timestamp":1661558400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Polish National Science Centre","award":["UMO-2019\/33\/B\/NZ7\/01608"],"award-info":[{"award-number":["UMO-2019\/33\/B\/NZ7\/01608"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The series of C2-symmetric biaryl core-based non-racemic bisphosphines possessing substituents of different electronic properties: both EDG and EWG were obtained in a short sequence of good yielding transformations, started from commercial 1,3-dimethyl-2-nitrobenzene. Several different approaches leading to the desirable ligands were practically evaluated. Notably, the synthesis of the entire series of ligands could be performed with the utilization of a single early-stage precursor DIDAB (6,6\u2032-diiodo-2,2\u2032,4,4\u2032-tetramethylbiphenyl-3,3\u2032-diamine), which could be easily obtained in enantiomerically pure form. The obtained compounds at concentrations of 50 and 200 \u00b5M showed various biological activity against normal human dermal fibroblast, ranging from inactivity through time-dependent action and ending up with high toxicity.<\/jats:p>","DOI":"10.3390\/molecules27175504","type":"journal-article","created":{"date-parts":[[2022,8,29]],"date-time":"2022-08-29T03:34:56Z","timestamp":1661744096000},"page":"5504","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["A Modular Approach to Atropisomeric Bisphosphines of Diversified Electronic Density on Phosphorus Atoms"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5571-1593","authenticated-orcid":false,"given":"Oleg M.","family":"Demchuk","sequence":"first","affiliation":[{"name":"Institute of Biological Sciences, Faculty of Science and Health, The John Paul II Catholic University of Lublin, Konstantyn\u00f3w 1J\/4.03, 20-708 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Aleksandra","family":"Martyna","sequence":"additional","affiliation":[{"name":"Institute of Biological Sciences, Faculty of Science and Health, The John Paul II Catholic University of Lublin, Konstantyn\u00f3w 1J\/4.03, 20-708 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-0345-639X","authenticated-orcid":false,"given":"Mateusz","family":"Kwa\u015bnik","sequence":"additional","affiliation":[{"name":"Institute of Biological Sciences, Faculty of Science and Health, The John Paul II Catholic University of Lublin, Konstantyn\u00f3w 1J\/4.03, 20-708 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8292-7373","authenticated-orcid":false,"given":"Katarzyna","family":"Szwaczko","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Maria Curie-Sklodowska University in Lublin, Gliniana 33, 20-031 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dorota","family":"Strzelecka","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Maria Curie-Sklodowska University in Lublin, Gliniana 33, 20-031 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5765-4641","authenticated-orcid":false,"given":"Barbara","family":"Miros\u0142aw","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Maria Curie-Sklodowska University in Lublin, Gliniana 33, 20-031 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0969-4689","authenticated-orcid":false,"given":"Kazimierz Micha\u0142","family":"Pietrusiewicz","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Maria Curie-Sklodowska University in Lublin, Gliniana 33, 20-031 Lublin, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2043-487X","authenticated-orcid":false,"given":"Zofia","family":"Urbanczyk-Lipkowska","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44\/52, 01-224 Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,8,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"5384","DOI":"10.1002\/anie.200462661","article-title":"Atroposelective Synthesis of Axially Chiral Biaryl Compounds","volume":"44","author":"Bringmann","year":"2005","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3193","DOI":"10.1039\/b821092f","article-title":"Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling","volume":"38","author":"Kozlowski","year":"2009","journal-title":"Chem. Soc. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1021\/cr100155e","article-title":"Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products","volume":"111","author":"Bringmann","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"6398","DOI":"10.1002\/anie.200901719","article-title":"The Challenge of Atropisomerism in Drug Discovery","volume":"48","author":"Clayden","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"7005","DOI":"10.1021\/jm200584g","article-title":"Assessing Atropisomer Axial Chirality in Drug Discovery and Development","volume":"54","author":"LaPlante","year":"2011","journal-title":"J. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1562","DOI":"10.1039\/C4NP00121D","article-title":"A twist of nature\u2014The significance of atropisomers in biological systems","volume":"32","author":"Smyth","year":"2015","journal-title":"Nat. Prod. Rep."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2405","DOI":"10.1021\/cr970463w","article-title":"1,1\u2032-Binaphthyl Dimers, Oligomers, and Polymers: Molecular Recognition, Asymmetric Catalysis, and New Materials","volume":"98","author":"Pu","year":"1998","journal-title":"Chem. Rev."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"150","DOI":"10.1021\/ar200048d","article-title":"Enantioselective Fluorescent Sensors: A Tale of BINOL","volume":"45","author":"Pu","year":"2011","journal-title":"Acc. Chem. Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"5334","DOI":"10.1021\/jacs.8b01860","article-title":"Binaphthyl\u2013Bipyridyl Cyclic Dyads as a Chiroptical Switch","volume":"140","author":"Takaishi","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"3029","DOI":"10.1021\/cr020049i","article-title":"New Chiral Phosphorus Ligands for Enantioselective Hydrogenation","volume":"103","author":"Tang","year":"2003","journal-title":"Chem. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2315","DOI":"10.1002\/ejic.201090043","article-title":"Atropochiral C,X- and C,C-Chelating Carbon Ligands","volume":"2010","author":"Canac","year":"2010","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_12","unstructured":"Noyori, R. (1994). Asymmetric Catalysis in Organic Synthesis, Wiley."},{"key":"ref_13","first-page":"758","article-title":"Evaluation of efficiency of chiral atropisomeric phosphorus ligands in the asymmetric catalytic processes mediated by transition metal complexes Part 1: Evaluation of steric effects","volume":"66","author":"Demchuk","year":"2012","journal-title":"Chemik"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2119","DOI":"10.1016\/j.ccr.2007.07.020","article-title":"Recent advances in developing new axially chiral phosphine ligands for asymmetric catalysis","volume":"251","author":"Li","year":"2007","journal-title":"Coord. Chem. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"7932","DOI":"10.1021\/ja00547a020","article-title":"Synthesis of 2,2\u2032-bis(diphenylphosphino)-1,1\u2032-binaphthyl (BINAP), an atropisomeric chiral bis(triaryl)phosphine, and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of.alpha.-(acylamino)acrylic acids","volume":"102","author":"Miyashita","year":"1980","journal-title":"J. Am. Chem. Soc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1245","DOI":"10.1016\/S0040-4020(01)82411-X","article-title":"2, 2\u2032-bis(diphenylphosphino)-1, 1\u2032-binaphthyl(binap)","volume":"40","author":"Miyashita","year":"1984","journal-title":"Tetrahedron"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"629","DOI":"10.1021\/jo00355a012","article-title":"Practical synthesis of (R)- or (S)-2,2\u2032-bis(diarylphosphino)-1,1\u2032-binaphthyls (BINAPs)","volume":"51","author":"Takaya","year":"1986","journal-title":"J. Org. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"897","DOI":"10.1002\/hlca.19880710427","article-title":"Axially Dissymmetric Bis(triaryl)phosphines in the Biphenyl series: Synthesis of (6,6\u2032-dimethylbiphenyl-2,2\u2032-diyl)bis(diphenylphosphine) (\u2018BIPHEMP\u2019) and analogues, and their use in Rh(I)-catalyzed asymmetric isomerizations ofN,N-diethylnerylamine","volume":"71","author":"Schmid","year":"1988","journal-title":"Helv. Chim. Acta"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1324","DOI":"10.1107\/S0108270186092405","article-title":"[(+)-(R)-2,2\u2032-Bis(diphenylphosphino)-6,6\u2032-dimethylbiphenyl](8,9,10-trinorborna-2,5-diene)rhodium(I) tetrafluoroborate","volume":"42","author":"Svensson","year":"1986","journal-title":"Acta Crystallogr. Sect. C Cryst. Struct. Commun."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"670","DOI":"10.3891\/acta.chem.scand.43-0670","article-title":"2,2\u2032-Dimethyl-6,6\u2032-bis(diphenylphosphino)biphenyl (BIPHEMP) as a Chiral Ligand for Transition Metal Catalyzed Asymmetric Synthesis of Binaphthyls and for Asymmetric Hydrogenation. A Comparison with BINAP","volume":"43","author":"Frejd","year":"1989","journal-title":"Acta Chem. Scand."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"300","DOI":"10.1002\/adsc.200390025","article-title":"Synthesis and Applications of HexaPHEMP, a Novel Biaryl Diphosphine Ligand","volume":"345","author":"Henschke","year":"2003","journal-title":"Adv. Synth. Catal."},{"key":"ref_22","unstructured":"Cereghetti, M., Foricher, J., Heiser, B., and Schmid, R. (1990). Phosphorous Compounds. (EP0398132A2, EP0398132B1), Europian Patent."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"370","DOI":"10.1002\/hlca.19910740215","article-title":"Axially Dissymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6\u2032-Dimethoxybiphenyl-2,2\u2032-diyl)bis(diphenylphosphine)(\u2018MeO-BIPHEP\u2019) and Analoguesviaanortho-Lithiation\/IodinationUllmann-Reaction Approach","volume":"74","author":"Schmid","year":"1991","journal-title":"Helv. Chim. Acta"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1351\/pac199668010131","article-title":"New developments in enantioselective hydrogenation","volume":"68","author":"Schmid","year":"1996","journal-title":"Pure Appl. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2767","DOI":"10.1248\/cpb.39.2767","article-title":"Asymmetric Reactions Catalyzed by Chiral Metal Complexes. L. Synthesis of atropisomeric biphenylbisphosphine, 6,6\u2032-bis(dicyclohexylphosphino)-3,3\u2032-dimethoxy-2,2\u2032,4,4\u2032-tetramethyl-1,1\u2032-biphenyl and its use in rhodium(I)-catalyzed asymmetric hydrogenation","volume":"39","author":"Murata","year":"1991","journal-title":"Chem. Pharm. Bull."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1849","DOI":"10.1246\/cl.1989.1849","article-title":"Synthesis of Atropisomeric 2,2\u2032-Bis(dicyclohexylphosphino)-6,6\u2032-dimethyl-1,1\u2032-biphenyl (BICHEP) and Its Use in Rh(I)-catalyzed Asymmetric Hydrogenation of Prochiral Olefins","volume":"18","author":"Miyashita","year":"1989","journal-title":"Chem. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"12051","DOI":"10.1021\/ja005622z","article-title":"A Catalytic Asymmetric Suzuki Coupling for the Synthesis of Axially Chiral Biaryl Compounds","volume":"122","author":"Yin","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.1002\/poc.2998","article-title":"Relationship between structure and efficiency of atropisomeric phosphine ligands in homogeneous catalytic asymmetric hydrogenation","volume":"25","author":"Demchuk","year":"2012","journal-title":"J. Phys. Org. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1016\/S0957-4166(00)82304-6","article-title":"A new type of atropisomeric biphenylbisphosphine ligand, (R)-MOC-BIMOP and its use in efficient asymmetric hydrogenation of \u03b1-aminoketone and itaconic acid","volume":"3","author":"Yoshikawa","year":"1992","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2177","DOI":"10.1016\/j.tetasy.2004.05.043","article-title":"Synthesis of ortho-phenyl substituted MeO-BIPHEP ligand and its application in Rh-catalyzed asymmetric hydrogenation","volume":"15","author":"Wu","year":"2004","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1695","DOI":"10.1021\/ol0258435","article-title":"Anortho-Substituted BIPHEP Ligand and Its Applications in Rh-Catalyzed Hydrogenation of Cyclic Enamides","volume":"4","author":"Tang","year":"2002","journal-title":"Org. Lett."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"3843","DOI":"10.1016\/j.tetlet.2005.03.183","article-title":"Avoiding the classical resolution during the synthesis of MeO-BIPHEP and 3,3\u2032-disubstituted derivatives","volume":"46","author":"Gorobets","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"5799","DOI":"10.1073\/pnas.0307620101","article-title":"Asymmetric Catalysis Special Feature Part II: Chiral biphenyl diphosphines for asymmetric catalysis: Stereoelectronic design and industrial perspectives","volume":"101","author":"Jeulin","year":"2004","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"3597","DOI":"10.1016\/j.tetlet.2004.03.073","article-title":"Synthesis, resolution and applications of 3,3\u2032-bis(RO)-MeO-BIPHEP derivatives","volume":"45","author":"Gorobets","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1178","DOI":"10.1021\/op2001673","article-title":"Process Research on the Asymmetric Hydrogenation of a Benzophenone for Developing the Manufacturing Process of the Squalene Synthase Inhibitor TAK-475","volume":"15","author":"Goto","year":"2011","journal-title":"Org. Process Res. Dev."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2359","DOI":"10.1039\/a705106i","article-title":"Convenient and direct preparation of tertiary phosphines via nickel-catalysed cross-coupling","volume":"24","author":"Ager","year":"1997","journal-title":"Chem. Commun."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"3137","DOI":"10.1021\/jo972330g","article-title":"Preparation and Use of a Polymer Supported BINAP Hydrogenation Catalyst","volume":"63","author":"Bayston","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"10828","DOI":"10.1002\/chem.201101467","article-title":"Improved Syntheses of Phosphine Ligands by Direct Coupling of Diarylbromophosphine with Organometallic Reagents","volume":"17","author":"Liu","year":"2011","journal-title":"Chem.-Eur. J."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1080\/10426507.2015.1079197","article-title":"The utilization of chiral phosphorus ligands in atroposelective cross-coupling reactions","volume":"191","author":"Demchuk","year":"2016","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"633","DOI":"10.1351\/PAC-CON-10-08-06","article-title":"Rational design of novel ligands for environmentally benign cross-coupling reactions","volume":"83","author":"Demchuk","year":"2011","journal-title":"Pure Appl. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"3418","DOI":"10.1039\/C5CS00012B","article-title":"Recent advances and new concepts for the synthesis of axially stereoenriched biaryls","volume":"44","author":"Panossian","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"6617","DOI":"10.1002\/anie.201701849","article-title":"Atroposelective Synthesis of Axially Chiral Biaryls by Palladium-Catalyzed Asymmetric C\u2212H Olefination Enabled by a Transient Chiral Auxiliary","volume":"56","author":"Yao","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"11644","DOI":"10.1002\/chem.201500869","article-title":"Catalytic Kinetic Resolution of Biaryl Compounds","volume":"21","author":"Ma","year":"2015","journal-title":"Chem.-A Eur. J."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"e202115221","DOI":"10.1002\/ange.202115221","article-title":"Experimental and Computational Studies on the Directing Ability of Chalcogenoethers in Palladium-Catalyzed Atroposelective C\u2212H Olefination and Allylation","volume":"134","author":"Liao","year":"2022","journal-title":"Angew. Chemie"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"7322","DOI":"10.1021\/jacs.0c01963","article-title":"Michael Reaction Inspired Atroposelective Construction of Axially Chiral Biaryls","volume":"142","author":"Yan","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"3609","DOI":"10.1016\/j.tetasy.2004.09.032","article-title":"Chiral atropisomeric diiodobiphenyls\u2013enantiodifferentiation by the dirhodium method","volume":"15","author":"Moeller","year":"2004","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"600","DOI":"10.1246\/bcsj.61.600","article-title":"Halogenation Using Quaternary Ammonium Polyhalides. VII. Iodination of Aromatic Amines by Use of Benzyltrimethylammonium Dichloroiodate(1\u2212)","volume":"61","author":"Kajigaeshi","year":"1988","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"609","DOI":"10.1080\/00397919408012638","article-title":"New Experiments in the Reductive N-Alkylation and N-Peralkylation of Aromatic Amines","volume":"24","author":"Verardo","year":"1994","journal-title":"Synth. Commun."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"743","DOI":"10.1055\/s-1980-29198","article-title":"N-Permethylation of Primary and Secondary Aromatic Amines","volume":"1980","author":"Giumanini","year":"1980","journal-title":"Synthesis"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1002\/hc.21279","article-title":"New Insights into the Mechanism of Reduction of Tertiary Phosphine Oxides by Means of Phenylsilane","volume":"26","author":"Demchuk","year":"2015","journal-title":"Heteroat. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"620","DOI":"10.1002\/anie.197906201","article-title":"Asymmetric Hydrogenation of (Z)-\u03b1-(Acetylamino)-cinnamic Acid by a Rh\/norphos Catalyst","volume":"18","author":"Brunner","year":"1979","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"2339","DOI":"10.1016\/j.tetasy.2008.10.001","article-title":"A convenient application of the NMR and CD methodologies for the determination of enantiomeric ratio and absolute configuration of chiral atropoisomeric phosphine oxides","volume":"19","author":"Demchuk","year":"2008","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1097","DOI":"10.1080\/00387019208018219","article-title":"NMR Studies of Drugs. Enantiomeric Excess Determination ofN-acetylcathinone with Eu(HFC)3","volume":"25","author":"Benshafrut","year":"2006","journal-title":"Spectrosc. Lett."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1459","DOI":"10.1016\/S0957-4166(03)00207-6","article-title":"The classical Kagan\u2019s amides are still practical NMR chiral shift reagents: Determination of enantiomeric purity of P-chirogenic phospholene oxides","volume":"14","author":"Pakulski","year":"2003","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1085","DOI":"10.1248\/cpb.39.1085","article-title":"Synthesis of axially dissymmetric biphenylbisphosphine ligands, bimops and asymmetric hydrogenations of.BETA.-keto ester and.ALPHA.,.BETA.-unsaturated carboxylic acid catalyzed by their ruthenium (II) complexes","volume":"39","author":"Yamamoto","year":"1991","journal-title":"Chem. Pharm. Bull."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1445","DOI":"10.1248\/cpb.52.1445","article-title":"Preparation of Axially Chiral Biphenyl Diphosphine Ligands and Their Application in Asymmetric Hydrogenation","volume":"52","author":"Morimoto","year":"2004","journal-title":"Chem. Pharm. Bull."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"5343","DOI":"10.1016\/0040-4039(96)01089-1","article-title":"An efficient access to (R)- and (S)-6,6\u2032-dimethoxy-2,2\u2032-diiodo-1,1\u2032-biphenyl","volume":"37","author":"Cereghetti","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"4812","DOI":"10.1021\/ic00074a026","article-title":"Optical resolutions and chelating properties of (.+-.)-[2-(methylsulfinyl)ethyl]diphenylarsine and its phosphorus analog","volume":"32","author":"Chooi","year":"1993","journal-title":"Inorg. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1753","DOI":"10.1016\/0957-4166(96)00210-8","article-title":"NMR assignment of absolute configuration of a P-chiral diphosphine and mechanics of its stereoselective formation","volume":"7","author":"Aw","year":"1996","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history ofSHELX","volume":"64","author":"Sheldrick","year":"2007","journal-title":"Acta Crystallogr. Sect. A Found. Crystallogr."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"3441","DOI":"10.1021\/jo00911a031","article-title":"Thallium in organic synthesis. XXXIX. Convenient synthesis of nitroaryl iodides","volume":"40","author":"Taylor","year":"1975","journal-title":"J. Org. 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