{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,17]],"date-time":"2025-10-17T13:32:22Z","timestamp":1760707942751,"version":"build-2065373602"},"reference-count":67,"publisher":"Wiley","issue":"19","license":[{"start":{"date-parts":[[2008,5,15]],"date-time":"2008-05-15T00:00:00Z","timestamp":1210809600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2008,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Transition states associated with the C\u2013C bond\u2010formation step in proline\u2010catalyzed intramolecular aldol reactions of 1,7\u2010dialdehydes were studied using density functional theory methods (DFT), at the B3LYP\/6\u201031G(d,p) level. A polarizable continuum model (PCM) was used to describe solvent effects. Two reactive channels, corresponding to the anhydrous system or to the explicit inclusion of water have been analysed. Computational data allow us to rationalize the intramolecular aldol reaction experimental outcome, validating the proposed enamine\u2010based mechanism, as well as to suggest the importance of water in the control of the reaction stereoselectivity. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2008)<\/jats:p>","DOI":"10.1002\/ejoc.200800222","type":"journal-article","created":{"date-parts":[[2008,5,15]],"date-time":"2008-05-15T18:16:34Z","timestamp":1210875394000},"page":"3397-3402","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Mechanistic Study of Intramolecular Aldol Reactions of Dialdehydes"],"prefix":"10.1002","volume":"2008","author":[{"given":"Filipe J. S.","family":"Duarte","sequence":"first","affiliation":[]},{"given":"Eurico J.","family":"Cabrita","sequence":"additional","affiliation":[]},{"given":"Gernot","family":"Frenking","sequence":"additional","affiliation":[]},{"given":"A. Gil","family":"Santos","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2008,6,17]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200400650"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja952692a"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00130a005"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00432a044"},{"key":"e_1_2_6_6_2","unstructured":"\u00a0"},{"key":"e_1_2_6_7_2","unstructured":"Z. G.Hajos D. R.Parrich German Patent DE2102623 1971."},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00925a003"},{"key":"e_1_2_6_9_2","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197104961"},{"key":"e_1_2_6_11_2","unstructured":"U.Eder G.Sauer R.Weichert German Patent DE2014757 1971."},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)00346-8"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00030a046"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar50107a005"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.03.038"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00173a059"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)71440-7"},{"key":"e_1_2_6_19_2","unstructured":"\u00a0"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200790050"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(99)00174-3"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(76)80016-6"},{"key":"e_1_2_6_23_2","first-page":"499","author":"Agami C.","year":"1988","journal-title":"Bull. Soc. Chim. Fr."},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)91242-6"},{"key":"e_1_2_6_25_2","unstructured":"\u00a0"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0307979101"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja028634o"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460916"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0507620"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja011403h"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja011714s"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200351266"},{"key":"e_1_2_6_33_2","unstructured":"\u00a0"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390291"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2005.02.028"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol048777a"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)91590-5"},{"key":"e_1_2_6_38_2","unstructured":"\u00a0"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)00343-B"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00126a057"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200503387"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017774f"},{"key":"e_1_2_6_43_2","unstructured":"\u00a0"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja010037z"},{"key":"e_1_2_6_45_2","first-page":"1891","author":"Nyberg A. I.","year":"2004","journal-title":"Synlett"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.09.070"},{"key":"e_1_2_6_47_2","unstructured":"\u00a0"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo048894j"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0573312"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2007.01.025"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500470"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604952"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200603378"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200601392"},{"key":"e_1_2_6_55_2","unstructured":"\u00a0"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp020079p"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-002-0381-7"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1039\/b701688c"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.10.034"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja012417q"},{"key":"e_1_2_6_61_2","unstructured":"\u00a0"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1016\/0304-5102(86)85043-X"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1039\/C39850000441"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.10.072"},{"volume-title":"Density Functional Theory of Atoms and Molecules","year":"1989","author":"Parr R. G.","key":"e_1_2_6_65_2"},{"key":"e_1_2_6_66_2","unstructured":"M. J. Frisch G. W. Trucks H. B. Schlegel G. E. Scuseria M. A. Robb J. R. Cheeseman J. A. Montgomery Jr T. Vreven K. N. Kudin J. C. Burant J. M. Millam S. S. Iyengar J. Tomasi V. Barone B. Mennucci M. Cossi G. Scalmani N. Rega G. A. Petersson H. Nakatsuji M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai M. Klene X. Li J. E. Knox H. P. Hratchian J. B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R. E. Stratmann O. Yazyev A. J. Austin R. Cammi C. Pomelli J. W. Ochterski P. Y. Ayala K. Morokuma G. A. Voth P. Salvador J. J. Dannenberg V. G. Zakrzewski S. Dapprich A. D. Daniels M. C. Strain O. Farkas D. K. Malick A. D. Rabuck K. Raghavachari J. B. Foresman J. V. Ortiz Q. Cui A. G. Baboul S. Clifford J. Cioslowski B. B. Stefanov G. Liu A. Liashenko P. Piskorz I. Komaromi R. L. Martin D. J. Fox T. Keith M. A. Al\u2010Laham C. Y. Peng A. Nanayakkara M. Challacombe P. M. W. Gill B. Johnson W. Chen M. W. Wong C. Gonzalez J. A. Pople Gaussian 03 revision E.01 Gaussian Inc. Wallingford CT 2004."},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.1480445"}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fejoc.200800222","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.200800222","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T16:06:05Z","timestamp":1760544365000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.200800222"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,6,17]]},"references-count":67,"journal-issue":{"issue":"19","published-print":{"date-parts":[[2008,7]]}},"alternative-id":["10.1002\/ejoc.200800222"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.200800222","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"type":"print","value":"1434-193X"},{"type":"electronic","value":"1099-0690"}],"subject":[],"published":{"date-parts":[[2008,6,17]]},"assertion":[{"value":"2008-02-27","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2008-06-17","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}