{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:38:33Z","timestamp":1786977513094,"version":"build-2736575974"},"reference-count":73,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2014,11,20]],"date-time":"2014-11-20T00:00:00Z","timestamp":1416441600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2015,1,7]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The asymmetric reduction of\n                    <jats:italic>N<\/jats:italic>\n                    \u2010aryl imines derived from acetophenones by using Ru complexes bearing both a pybox (2,6\u2010bis(oxazoline)pyridine) and a monodentate phosphite ligand has been described. The catalysts show good activity with a diverse range of substrates, and deliver the amine products in very high levels of enantioselectivity (up to 99\u2009%) under both hydrogenation and transfer hydrogenation conditions in isopropanol. From deuteration studies, a very different labeling is observed under hydrogenation and transfer hydrogenation conditions, which demonstrates the different nature of the hydrogen source in both reactions.\n                  <\/jats:p>","DOI":"10.1002\/chem.201405276","type":"journal-article","created":{"date-parts":[[2014,11,20]],"date-time":"2014-11-20T16:58:52Z","timestamp":1416502732000},"page":"549-553","source":"Crossref","is-referenced-by-count":44,"title":["Highly Enantioselective Hydrogenation of\n                    <i>N<\/i>\n                    \u2010Aryl Imines Derived from Acetophenones by Using Ru\u2013Pybox Complexes under Hydrogenation or Transfer Hydrogenation Conditions in Isopropanol"],"prefix":"10.1002","volume":"21","author":[{"given":"Estefan\u00eda","family":"Men\u00e9ndez\u2010Pedregal","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"M\u00f3nica","family":"Vaquero","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elena","family":"Lastra","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pilar","family":"Gamasa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antonio","family":"Pizzano","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,11,20]]},"reference":[{"key":"e_1_2_3_1_2","unstructured":"For reviews on this topic see:"},{"key":"e_1_2_3_2_2","first-page":"1193","volume-title":"The Handbook of Homogeneous Hydrogenation, Vol.\u20053","author":"Spindler F.","year":"2007"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900719"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201000078"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100218m"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201202836"},{"key":"e_1_2_3_7_2","unstructured":"For some representative examples see:"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00099a012"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502482"},{"key":"e_1_2_3_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200502482"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja063444p"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja807188s"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200901630"},{"key":"e_1_2_3_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200901630"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja901961y"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200903418"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201000733"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201100878"},{"key":"e_1_2_3_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201100878"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201200464"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200800196"},{"key":"e_1_2_3_19_2","unstructured":"However a remarkable broad scope in the asymmetric transfer hydrogenation of imines has been achieved with the HCOOH\/NEt3mixture as a reducing agent see:"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja960364k"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201002944"},{"key":"e_1_2_3_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201002944"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201204194"},{"key":"e_1_2_3_23_2","unstructured":"For reviews on this topic see:"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar9502341"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/B513396C"},{"key":"e_1_2_3_25_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2014.03.140"},{"key":"e_1_2_3_26_2","unstructured":"\u00a0"},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201102426"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo4014386"},{"key":"e_1_2_3_29_2","unstructured":"\u00a0"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol302079q"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1244466"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201002456"},{"key":"e_1_2_3_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201002456"},{"key":"e_1_2_3_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201301115"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20020703)8:13<2955::AID-CHEM2955>3.0.CO;2-Q"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.81.1053"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200305170"},{"key":"e_1_2_3_37_2","unstructured":"\u00a0"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200390011"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201203193"},{"key":"e_1_2_3_40_2","unstructured":"For a related study of the deuteration of substrate3\u2009aunder hydrogenation and transfer hydrogenation conditions see ref.\u2005[13a]."},{"key":"e_1_2_3_41_2","unstructured":"For studies covering isotopic effects in the hydrogenation\/transfer hydrogenation of ketones see:"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200600475"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200800246"},{"key":"e_1_2_3_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9043104"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/om001054k"},{"key":"e_1_2_3_46_2","unstructured":"In studies on the hydrogenation oftrans\u20104\u2010phenyl\u2010buten\u20103\u2010ene\u20102\u2010one the preferential reduction of the C\uf8feO bond has been used as evidence in favor of an outer\u2010sphere mechanism. For examples see:"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/om101152m"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/om300108p"},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201304770"},{"key":"e_1_2_3_50_2","unstructured":"\u00a0"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/B303258B"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/B410698A"},{"key":"e_1_2_3_53_2","doi-asserted-by":"publisher","DOI":"10.1039\/b515269k"},{"key":"e_1_2_3_54_2","unstructured":"For outer\u2010sphere mechanism proposals see:"},{"key":"e_1_2_3_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja044450t"},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja056402u"},{"key":"e_1_2_3_57_2","unstructured":"For studies reflecting the high reactivity of related Ru\u2013amide complexes with alcohols see:"},{"key":"e_1_2_3_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja8034812"},{"key":"e_1_2_3_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja202732q"},{"key":"e_1_2_3_60_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2004.04.007"},{"key":"e_1_2_3_61_2","unstructured":"In a detailed study of a cationic Ru catalyst for hydrogenation based on an amino\u2010carbene ligand an inner\u2010sphere pathway and a key amine dissociation step facilitated by the alcoxide ligand have been proposed (Ref.\u2005[17a]). In the present case the absence of chelation should also favor the release of the amine product."},{"key":"e_1_2_3_62_2","unstructured":"In the hydrogenation and transfer hydrogenation of ketones catalyzed by the Ru tetradentate diphosphane diamine complex similar alkoxides have been postulated as intermediates (Ref.\u2005[18]). From the latter regeneration of the hydride by \u03b2\u2010elimination (transfer hydrogenation) or by reaction with hydrogen (hydrogenation) have been proposed."},{"key":"e_1_2_3_63_2","unstructured":"Several cases of catalysts promoting both hydrogenation and transfer hydrogenation of ketones are known see:"},{"key":"e_1_2_3_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200304884"},{"key":"e_1_2_3_65_2","unstructured":"Ref.\u2005[15b];"},{"key":"e_1_2_3_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800339"},{"key":"e_1_2_3_66_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200800339"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201405276","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201405276","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T12:58:42Z","timestamp":1760273922000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201405276"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,11,20]]},"references-count":73,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2015,1,7]]}},"alternative-id":["10.1002\/chem.201405276"],"URL":"https:\/\/doi.org\/10.1002\/chem.201405276","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,11,20]]}}}