{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,30]],"date-time":"2025-12-30T23:22:28Z","timestamp":1767136948906,"version":"build-2238731810"},"reference-count":50,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2011,11,30]],"date-time":"2011-11-30T00:00:00Z","timestamp":1322611200000},"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":[[2012,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The aim of this work was to immobilize an Arylid\u2010BOX ligand on solid supports either by covalent attachment (to Wang resin) or by noncovalent attachment (on MK10 and SiO\n                    <jats:sub>2<\/jats:sub>\n                    ) and to evaluate the products in the catalytic asymmetric cyclopropanation (CACP) of styrene in the presence of Cu\n                    <jats:sup>I<\/jats:sup>\n                    and Cu\n                    <jats:sup>II<\/jats:sup>\n                    . The synthetic strategy used to obtain the target functionalized Arylid\u2010BOX furnished a new, partially hydrogenated, Arylid\u2010BOX derivative. Evaluation of this ligand in the catalytic asymmetric cyclopropanation of styrene in the presence of Cu\n                    <jats:sup>I<\/jats:sup>\n                    gave a highest\n                    <jats:italic>ee<\/jats:italic>\n                    of 68\u2009%, a result better than that obtained for the nonhydrogenated Arylid\u2010BOX ligand. The new ligand was grafted to Wang resin; a loading of 0.321 mmol of ligand per gram of polymer could be obtained. [Cu(CH\n                    <jats:sub>3<\/jats:sub>\n                    CN)\n                    <jats:sub>4<\/jats:sub>\n                    ]PF\n                    <jats:sub>6<\/jats:sub>\n                    or Cu(OTf)\n                    <jats:sub>2<\/jats:sub>\n                    were used in the CACP of styrene with CH\n                    <jats:sub>2<\/jats:sub>\n                    Cl\n                    <jats:sub>2<\/jats:sub>\n                    or toluene as solvents. A highest\n                    <jats:italic>ee<\/jats:italic>\n                    of 71\u2009% was obtained and the catalyst could be recycled and reused up to four times. In the case of the heterogeneous CACP in the presence of [Cu(CH\n                    <jats:sub>3<\/jats:sub>\n                    CN)\n                    <jats:sub>4<\/jats:sub>\n                    ]PF\n                    <jats:sub>6<\/jats:sub>\n                    and toluene, the yields,\n                    <jats:italic>ee<\/jats:italic>\n                    s, des, and selectivities were maintained over the four cycles. This heterogeneous catalyst was shown to be very similar to the homogeneous catalyst with regard to selectivity and activity. In the case of noncovalent immobilization, both Cu\n                    <jats:sup>I<\/jats:sup>\n                    and Cu\n                    <jats:sup>II<\/jats:sup>\n                    Arylid\u2010BOX complexes were immobilized on Montmorillonite K10 (MK10) and silica gel through noncovalent interactions. The obtained results depended on the natures both of the chiral ligand and of the support. In the case of MK10, enantioselectivities of 62\u2009%\n                    <jats:italic>ee<\/jats:italic>\n                    (\n                    <jats:italic>trans<\/jats:italic>\n                    \u2010cyclopropane) and 65\u2009%\n                    <jats:italic>ee<\/jats:italic>\n                    (\n                    <jats:italic>cis<\/jats:italic>\n                    \u2010cyclopropane) could be achieved, whereas in the case of the silica\u2010gel\u2010supported catalyst, enantioselectivities of 50\u2009%\n                    <jats:italic>ee<\/jats:italic>\n                    (\n                    <jats:italic>trans<\/jats:italic>\n                    \u2010cyclopropane) and 43\u2009%\n                    <jats:italic>ee<\/jats:italic>\n                    (\n                    <jats:italic>cis<\/jats:italic>\n                    \u2010cyclopropane) were obtained.\n                  <\/jats:p>","DOI":"10.1002\/ejoc.201100781","type":"journal-article","created":{"date-parts":[[2011,12,1]],"date-time":"2011-12-01T15:05:36Z","timestamp":1322751936000},"page":"518-528","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Covalent and Noncovalent Immobilization of Arylid\u2010BOX Ligands and Their Derivatives: Evaluation in the Catalytic Asymmetric Cyclopropanation of Styrenes"],"prefix":"10.1002","volume":"2012","author":[{"given":"Elisabete P.","family":"Carreiro","sequence":"first","affiliation":[]},{"given":"Nuno M. M.","family":"Moura","sequence":"additional","affiliation":[]},{"given":"Anthony J.","family":"Burke","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2011,11,30]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1351\/pac200476030679"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.matsci.35.100303.122029"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1351\/pac200173081319"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/B806643B"},{"key":"e_1_2_6_6_2","unstructured":"\u00a0"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.apcatb.2003.11.012"},{"key":"e_1_2_6_8_2","unstructured":"V. S. Gerard F. Notheisz 2000 Heterogeneous Catalysis in Organic Chemistry Elsevier"},{"key":"e_1_2_6_9_2","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020008m"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2007.10.011"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr800363y"},{"key":"e_1_2_6_13_2","unstructured":"\u00a0"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(97)00593-4"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0505324"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr040642v"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr800400z"},{"key":"e_1_2_6_18_2","unstructured":"\u00a0"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0066633"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0159338"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(02)00259-7"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/b306483b"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2005.02.026"},{"key":"e_1_2_6_24_2","unstructured":"\u00a0"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200505197"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200606121"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0gc00775g"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(97)00242-5"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200305739"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.03.001"},{"key":"e_1_2_6_31_2","unstructured":"\u00a0"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2008.12.046"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2008.12.046"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.inoche.2006.04.031"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2007.06.068"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2009.04.005"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900669"},{"key":"e_1_2_6_38_2","first-page":"2589","volume":"16","author":"Yuryev R.","year":"2009","journal-title":"Synlett"},{"key":"e_1_2_6_39_2","unstructured":"S. C. Gertrudes A. J. Burke unpublished results."},{"key":"e_1_2_6_40_2","unstructured":"N. M. M. Moura B.Sc. Thesis Universidade de \u00c9vora Portugal 2006."},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja002246"},{"key":"e_1_2_6_42_2","unstructured":"E. P. Carreiro Ph.D. Thesis(European) Universidade de \u00c9vora Portugal 2010."},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00415a045"},{"key":"e_1_2_6_44_2","unstructured":"\u00a0"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1566-7367(01)00027-9"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcat.2008.06.028"},{"key":"e_1_2_6_47_2","unstructured":"\u00a0"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja003695c"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200601358"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00065a020"}],"updated-by":[{"DOI":"10.1002\/ejoc.201200186","type":"correction","label":"Correction","source":"publisher","updated":{"date-parts":[[2012,3,1]],"date-time":"2012-03-01T00:00:00Z","timestamp":1330560000000}}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fejoc.201100781","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.201100781","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T18:38:39Z","timestamp":1760553519000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.201100781"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2011,11,30]]},"references-count":50,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2012,1]]}},"alternative-id":["10.1002\/ejoc.201100781"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.201100781","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"value":"1434-193X","type":"print"},{"value":"1099-0690","type":"electronic"}],"subject":[],"published":{"date-parts":[[2011,11,30]]},"assertion":[{"value":"2011-06-01","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2011-11-30","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}