{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T00:40:56Z","timestamp":1760316056280,"version":"build-2065373602"},"reference-count":49,"publisher":"Wiley","issue":"51","license":[{"start":{"date-parts":[[2018,8,17]],"date-time":"2018-08-17T00:00:00Z","timestamp":1534464000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003549","name":"Orsz\u00e1gos Tudom\u00e1nyos Kutat\u00e1si Alapprogramok","doi-asserted-by":"publisher","award":["K112442","K115731"],"award-info":[{"award-number":["K112442","K115731"]}],"id":[{"id":"10.13039\/501100003549","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005909","name":"Nemzeti Fejleszt\u00e9si Miniszt\u00e9rium","doi-asserted-by":"publisher","award":["GINOP-2.3.2-15-2016-00012"],"award-info":[{"award-number":["GINOP-2.3.2-15-2016-00012"]}],"id":[{"id":"10.13039\/501100005909","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":[[2018,9,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A library of monoterpene\u2010based aminodiols was synthesized and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The reduction of a bicyclic \u03b1\u2010methylene ketone, derived from natural (\u2212)\u2010limonene followed by epoxidation, gave the key epoxy alcohol intermediate. Ring opening of the oxirane ring with primary amines induced by lithium perchlorate afforded the required aminodiols. Substituent\u2010dependent ring closure of the secondary aminodiols with formaldehyde resulted in both spirooxazolidines and a fused 1,3\u2010oxazine. Cyclization reactions of the studied aminodiols, resulting in spirocyclic oxazolidines and an isomeric perhydro\u20101,3\u2010oxazine\u2010fused compound along with the possible iminium intermediates, were analyzed by a systematic series of comparative DFT models performed at the B3LYP\/6\u201031+G(d,p) level of theory.<\/jats:p>","DOI":"10.1002\/chem.201802484","type":"journal-article","created":{"date-parts":[[2018,6,20]],"date-time":"2018-06-20T10:49:47Z","timestamp":1529491787000},"page":"13607-13615","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Regio\u2010 and Stereoselective Synthesis of Bicyclic Limonene\u2010Based Chiral Aminodiols and Spirooxazolidines"],"prefix":"10.1002","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8296-887X","authenticated-orcid":false,"given":"Tam Minh","family":"Le","sequence":"first","affiliation":[{"name":"Institute of Pharmaceutical Chemistry University of Szeged  H-6720 Szeged E\u00f6tv\u00f6s utca 6 Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2107-7309","authenticated-orcid":false,"given":"Antal","family":"Cs\u00e1mpai","sequence":"additional","affiliation":[{"name":"Institute of Chemistry E\u00f6tv\u00f6s Lor\u00e1nd University  P.O. Box 32 H-1518 Budapest\u2212112 Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ferenc","family":"F\u00fcl\u00f6p","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Chemistry University of Szeged  H-6720 Szeged E\u00f6tv\u00f6s utca 6 Hungary"},{"name":"MTA-SZTE Stereochemistry Research Group Hungarian Academy of Science  E\u00f6tv\u00f6s u. 6 H-6720 Szeged Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2432-8409","authenticated-orcid":false,"given":"Zsolt","family":"Szakonyi","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Chemistry University of Szeged  H-6720 Szeged E\u00f6tv\u00f6s utca 6 Hungary"},{"name":"Interdisciplinary Centre of Natural Products University of Szeged  H 6720 Szeged Hungary"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,8,17]]},"reference":[{"volume-title":"Catalysis in Asymmetric Synthesis","year":"2009","author":"Caprio V.","key":"e_1_2_7_1_1"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200505057"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.drudis.2006.11.004"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2005.12.011"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol006181r"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2017.03.050"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2011.06.013"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201600749"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo061547k"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2016.04.009"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(00)00230-5"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo034251c"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo960047w"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1990-21244"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/0957-4166(94)00359-J"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo982403b"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(00)00149-6"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00275-7"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2003.08.029"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)01495-2"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2014.10.101"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr000411y"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2014.09.007"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol050829o"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2007.03.027"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol062752p"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2010.02.012"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200701010"},{"key":"e_1_2_7_29_1","unstructured":"W. F.Erman C. D.Broaddus Metalation of Limonene and Syntheses of LimoneneDerivatives US3658925 A 1972."},{"key":"e_1_2_7_30_1","unstructured":"D. E.Chastain N.Mody G.Majetich Method of Preparing Selected Monocyclic Monoterpenes US5574195 A 1996."},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-2952(98)00349-9"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.10.289"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2010.09.009"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201701299"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01350a042"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1071\/CH01168"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1006\/jcat.2000.3104"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2010.11.079"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2007.07.065"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo062674j"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC02179K"},{"key":"e_1_2_7_42_1","doi-asserted-by":"crossref","first-page":"33","DOI":"10.3998\/ark.5550190.0009.305","author":"Szakonyi Z.","year":"2007","journal-title":"ARKIVOC"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23040771"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100096a001"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.1674902"},{"key":"e_1_2_7_46_1","unstructured":"Gaussian\u200509 (Revision\u2005A.02) M.\u2005J. Frisch G.\u2005W. Trucks H.\u2005B. Schlegel G.\u2005E. Scuseria M.\u2005A. Robb J.\u2005R. Cheeseman G. Scalmani V. Barone G.\u2005A. Petersson H. Nakatsuji X. Li M. Caricato A. Marenich J. Bloino B.\u2005G. Janesko R. Gomperts B. Mennucci H.\u2005P. Hratchian J.\u2005V. Ortiz A.\u2005F. Izmaylov J.\u2005L. Sonnenberg D. Williams-Young F. Ding F. Lipparini F. Egidi J. Goings B. Peng A. Petrone T. Henderson D. Ranasinghe V.\u2005G. Zakrzewski J. Gao N. Rega G. Zheng W. Liang M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven K. Throssell J.\u2005A. Montgomery \u2005Jr. 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 J.\u2005M. Millam M. Klene C. Adamo R. Cammi J.\u2005W. Ochterski R.\u2005L. Martin K. Morokuma O. Farkas J.\u2005B. Foresman and D.\u2005J. Fox Gaussian Inc. Wallingford CT 2016."},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/ijch.199300051"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo034007l"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo060964u"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201802484","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201802484","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T13:56:43Z","timestamp":1760277403000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201802484"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,8,17]]},"references-count":49,"journal-issue":{"issue":"51","published-print":{"date-parts":[[2018,9,12]]}},"alternative-id":["10.1002\/chem.201802484"],"URL":"https:\/\/doi.org\/10.1002\/chem.201802484","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2018,8,17]]},"assertion":[{"value":"2018-05-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-08-17","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}