{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T03:43:01Z","timestamp":1789443781475,"version":"build-2803163510"},"reference-count":111,"publisher":"Wiley","issue":"45","license":[{"start":{"date-parts":[[2022,6,23]],"date-time":"2022-06-23T00:00:00Z","timestamp":1655942400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["ME 4267\/3-1 and ME 4267\/5-1"],"award-info":[{"award-number":["ME 4267\/3-1 and ME 4267\/5-1"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["EXC-2033"],"award-info":[{"award-number":["EXC-2033"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2022,8,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>In this study, we characterize the dynamic stereochemistry of a biphenyl\u20102,2\u2019\u2010bis(proline amide) catalyst in chloroform and DMSO as representative weakly and strongly hydrogen bonding solvents. Using vibrational circular dichroism (VCD) spectroscopy and density functional theory (DFT) based spectra calculations, we show that the preferred axial stereochemistry of the catalyst is determined by solute\u2010solvent interactions. Explicitly considering solvation with DMSO molecules is found to be essential to correctly predict the conformational preferences of the catalyst. Furthermore, we investigate the stereochemistry of the corresponding enamines and imidazolidinones that are formed upon reaction with isovaleraldehyde. The enamines are found to rapidly convert to <jats:italic>endo<\/jats:italic>\u2010imidazolidinones and the thermodynamically favored <jats:italic>exo<\/jats:italic>\u2010imidazolidinones are formed only slowly. The present study demonstrates that the stereochemistry of these imidazolidinones can be deduced directly from the VCD spectra analysis without any further detailed analysis of NMR spectra. Hence, we herein exemplify the use of VCD spectroscopy for an in\u2005situ characterization of intermediates relevant in asymmetric catalysts.<\/jats:p>","DOI":"10.1002\/chem.202201317","type":"journal-article","created":{"date-parts":[[2022,5,25]],"date-time":"2022-05-25T05:12:07Z","timestamp":1653455527000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Dynamic Stereochemistry of a Biphenyl\u2010Bisprolineamide Model Catalyst and its Imidazolidinone Intermediates"],"prefix":"10.1002","volume":"28","author":[{"given":"Tino P.","family":"Golub","sequence":"first","affiliation":[{"name":"Ruhr Universit\u00e4t Bochum Fakult\u00e4t f\u00fcr Chemie und Biochemie Organische Chemie II  Universit\u00e4tsstra\u00dfe 150 44801 Bochum Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Malte","family":"Fe\u00dfner","sequence":"additional","affiliation":[{"name":"Ruhr Universit\u00e4t Bochum Fakult\u00e4t f\u00fcr Chemie und Biochemie Organische Chemie II  Universit\u00e4tsstra\u00dfe 150 44801 Bochum Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4640-6260","authenticated-orcid":false,"given":"Elric","family":"Engelage","sequence":"additional","affiliation":[{"name":"Ruhr Universit\u00e4t Bochum Fakult\u00e4t f\u00fcr Chemie und Biochemie Organische Chemie II  Universit\u00e4tsstra\u00dfe 150 44801 Bochum Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4106-1905","authenticated-orcid":false,"given":"Christian","family":"Merten","sequence":"additional","affiliation":[{"name":"Ruhr Universit\u00e4t Bochum Fakult\u00e4t f\u00fcr Chemie und Biochemie Organische Chemie II  Universit\u00e4tsstra\u00dfe 150 44801 Bochum Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,6,23]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/9781119976516"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1201\/b12278"},{"key":"e_1_2_8_4_2","first-page":"421","volume-title":"Vibrational Optical Activity: From Small Chiral Molecules to Protein Pharmaceuticals and Beyond, in Frontiers and Advances in Molecular Spectroscopy","author":"Nafie L. A.","year":"2018"},{"key":"e_1_2_8_5_1","unstructured":"\u00a0"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5NP00027K"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b00466"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0NP00025F"},{"key":"e_1_2_8_9_1","unstructured":"\u00a0"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.3389\/fchem.2016.00009"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CP55018D"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic4031766"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.4767401"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.3431540"},{"key":"e_1_2_8_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp801996m"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/bip.22986"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.201101003"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20825"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/b703368k"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CP03869E"},{"key":"e_1_2_8_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CP01695J"},{"key":"e_1_2_8_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CP02491J"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic502661u"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp4114738"},{"key":"e_1_2_8_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp303891x"},{"key":"e_1_2_8_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20817"},{"key":"e_1_2_8_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.saa.2020.119094"},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcb.0c01483"},{"key":"e_1_2_8_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CP03106F"},{"key":"e_1_2_8_30_1","unstructured":"\u00a0"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CP05688C"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20803"},{"key":"e_1_2_8_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbamem.2013.12.005"},{"key":"e_1_2_8_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp311151h"},{"key":"e_1_2_8_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.22045"},{"key":"e_1_2_8_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC06861J"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC02866H"},{"key":"e_1_2_8_38_1","unstructured":"\u00a0"},{"key":"e_1_2_8_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC00932J"},{"key":"e_1_2_8_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CP05457K"},{"key":"e_1_2_8_41_1","unstructured":"\u00a0"},{"key":"e_1_2_8_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcb.8b05928"},{"key":"e_1_2_8_43_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CP02049J"},{"key":"e_1_2_8_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpcb.6b05897"},{"key":"e_1_2_8_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CP06030H"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CP01656J"},{"key":"e_1_2_8_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CP01407A"},{"key":"e_1_2_8_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201703643"},{"key":"e_1_2_8_49_1","unstructured":"\u00a0"},{"key":"e_1_2_8_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202000876"},{"key":"e_1_2_8_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202204624"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501271"},{"key":"e_1_2_8_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201501271"},{"key":"e_1_2_8_53_1","unstructured":"\u00a0"},{"key":"e_1_2_8_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CP02395F"},{"key":"e_1_2_8_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201804230"},{"key":"e_1_2_8_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201602097"},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201905614"},{"key":"e_1_2_8_58_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CP04497D"},{"key":"e_1_2_8_59_1","unstructured":"\u00a0"},{"key":"e_1_2_8_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201503920"},{"key":"e_1_2_8_60_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201503920"},{"key":"e_1_2_8_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201303982"},{"key":"e_1_2_8_62_2","doi-asserted-by":"publisher","DOI":"10.1039\/C0CC02417A"},{"key":"e_1_2_8_63_2","doi-asserted-by":"publisher","DOI":"10.1039\/b514296m"},{"key":"e_1_2_8_64_1","unstructured":"\u00a0"},{"key":"e_1_2_8_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200800432"},{"key":"e_1_2_8_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200890216"},{"key":"e_1_2_8_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200790050"},{"key":"e_1_2_8_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00320"},{"key":"e_1_2_8_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03420"},{"key":"e_1_2_8_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja111544b"},{"key":"e_1_2_8_71_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1sc00274k"},{"key":"e_1_2_8_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0684016"},{"key":"e_1_2_8_73_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.1052"},{"key":"e_1_2_8_74_1","unstructured":"\u00a0"},{"key":"e_1_2_8_75_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200300906"},{"key":"e_1_2_8_76_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201300087"},{"key":"e_1_2_8_77_2","volume-title":"Dynamic Stereochemistry of Chiral Compounds: Principles and Applications","author":"Wolf C.","year":"2007"},{"key":"e_1_2_8_78_1","unstructured":"\u00a0"},{"key":"e_1_2_8_79_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2638"},{"key":"e_1_2_8_80_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201901175"},{"key":"e_1_2_8_80_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201901175"},{"key":"e_1_2_8_81_2","doi-asserted-by":"publisher","DOI":"10.1038\/385613a0"},{"key":"e_1_2_8_82_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201801048"},{"key":"e_1_2_8_82_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201801048"},{"key":"e_1_2_8_83_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2002-34228"},{"key":"e_1_2_8_84_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc34320g"},{"key":"e_1_2_8_85_1","unstructured":"\u00a0"},{"key":"e_1_2_8_86_2","doi-asserted-by":"publisher","DOI":"10.1039\/b917554g"},{"key":"e_1_2_8_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol070002p"},{"key":"e_1_2_8_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201201306"},{"key":"e_1_2_8_89_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-939701"},{"key":"e_1_2_8_90_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0029-1217808"},{"key":"e_1_2_8_91_2","doi-asserted-by":"publisher","DOI":"10.3998\/ark.5550190.0012.313"},{"key":"e_1_2_8_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo800773q"},{"key":"e_1_2_8_93_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2006.02.004"},{"key":"e_1_2_8_94_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-958924"},{"key":"e_1_2_8_95_1","unstructured":"Gaussian 09 Rev E.01 M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone B. Mennucci G.\u2005A. Petersson H. Nakatsuji M. Caricato X. Li H.\u2005P. Hratchian A.\u2005F. Izmaylov J. Bloino G. Zheng J.\u2005L. Sonnenberg M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven J.\u2005J.\u2005A. Montgomery J.\u2005E. Peralta F. Ogliaro M. Bearpark J.\u2005J. Heyd E. Brothers K.\u2005N. Kudin V.\u2005N. Staroverov T. Keith R. Kobayashi J. Normand K. Raghavachari A. Rendell J.\u2005C. Burant S.\u2005S. Iyengar J. Tomasi M. Cossi N. Rega J.\u2005M. Millam M. Klene J.\u2005E. Knox J.\u2005B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R.\u2005E. Stratmann O. Yazyev A.\u2005J. Austin R. Cammi C. Pomelli J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma V.\u2005G. Zakrzewski G.\u2005A. Voth P. Salvador J.\u2005J. Dannenberg S. Dapprich A.\u2005D. Daniels O. Farkas J.\u2005B. Foresman J.\u2005V. Ortiz J. Cioslowski D.\u2005J. Fox Wallingford CT USA 2013."},{"key":"e_1_2_8_96_1","unstructured":"\u00a0"},{"key":"e_1_2_8_97_2","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20984"},{"key":"e_1_2_8_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9904009"},{"key":"e_1_2_8_99_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202014130"},{"key":"e_1_2_8_99_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202014130"},{"key":"e_1_2_8_100_1","unstructured":"CYLview 1.0b C.\u2005Y. Legault Universit\u00e9 de Sherbrooke 2009."},{"key":"e_1_2_8_101_1","unstructured":"CrysAlisPro 2018."},{"key":"e_1_2_8_102_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889899006020"},{"key":"e_1_2_8_103_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767307043930"},{"key":"e_1_2_8_104_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889811043202"},{"key":"e_1_2_8_105_1","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1002\/0470024763.ch5","volume-title":"NMR Spectra, in The Chemistry of Enamines","author":"Chiara J. L.","year":"1994"},{"key":"e_1_2_8_106_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201201174"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202201317","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202201317","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202201317","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T18:22:48Z","timestamp":1760293368000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202201317"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,6,23]]},"references-count":111,"journal-issue":{"issue":"45","published-print":{"date-parts":[[2022,8,10]]}},"alternative-id":["10.1002\/chem.202201317"],"URL":"https:\/\/doi.org\/10.1002\/chem.202201317","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,6,23]]},"assertion":[{"value":"2022-04-28","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-06-23","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202201317"}}