{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T08:58:16Z","timestamp":1791104296094,"version":"4.1.0"},"reference-count":67,"publisher":"Wiley","issue":"13","license":[{"start":{"date-parts":[[2008,3,13]],"date-time":"2008-03-13T00:00:00Z","timestamp":1205366400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2008,3,13]],"date-time":"2008-03-13T00:00:00Z","timestamp":1205366400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2008,4,28]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Reduction of allylic alcohols can be promoted efficiently by the supported ruthenium catalyst Ru(OH)\n                    <jats:sub>\n                      <jats:italic>x<\/jats:italic>\n                    <\/jats:sub>\n                    \/Al\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    . Various allylic alcohols were converted to saturated alcohols in excellent yields by using 2\u2010propanol without any additives. This Ru(OH)\n                    <jats:sub>\n                      <jats:italic>x<\/jats:italic>\n                    <\/jats:sub>\n                    \/Al\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    \u2010catalyzed reduction of a dienol proceeds only at the allylic double bond to afford the corresponding enol, and chemoselective isomerization and reduction can be realized under similar conditions. The catalysis is truly heterogeneous and the high catalytic performance can be maintained during at least three recycles of the Ru(OH)\n                    <jats:sub>\n                      <jats:italic>x<\/jats:italic>\n                    <\/jats:sub>\n                    \/Al\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    catalyst. The transformation of allylic alcohols to saturated alcohols consists of three sequential reactions: oxidation of allylic alcohols to \u03b1,\u03b2\u2010unsaturated carbonyl compounds; reduction of \u03b1,\u03b2\u2010unsaturated carbonyl compounds to saturated carbonyl compounds; and reduction of saturated carbonyl compounds to saturated alcohols.\n                  <\/jats:p>","DOI":"10.1002\/chem.200701917","type":"journal-article","created":{"date-parts":[[2008,3,13]],"date-time":"2008-03-13T08:16:29Z","timestamp":1205396189000},"page":"4104-4109","source":"Crossref","is-referenced-by-count":50,"title":["Synthetic Scope of Ru(OH)\n                    <sub>\n                      <i>x<\/i>\n                    <\/sub>\n                    \/Al\n                    <sub>2<\/sub>\n                    O\n                    <sub>3<\/sub>\n                    \u2010Catalyzed Hydrogen\u2010Transfer Reactions: An Application to Reduction of Allylic Alcohols by a Sequential Process of Isomerization\/Meerwein\u2013Ponndorf\u2013Verley\u2010Type Reduction"],"prefix":"10.1002","volume":"14","author":[{"given":"Jung\u2005Won","family":"Kim","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takeshi","family":"Koike","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miyuki","family":"Kotani","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazuya","family":"Yamaguchi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Noritaka","family":"Mizuno","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2008,3,13]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","volume-title":"March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure","author":"Smith M. 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L.","year":"1965"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.apcata.2004.08.025"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200390000"},{"key":"e_1_2_6_9_2","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/b501096a"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja038804c"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0105257"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1169(01)00316-8"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1169(00)00146-1"},{"key":"e_1_2_6_15_2","unstructured":"Dry Pd\/C and Pt\/C catalysts must be handled carefully because of the risk of ignition due to electrical discharge by friction. The results for the hydrogenation of allylic alcohols with classical hydrogenation catalysts are summarized in Scheme\u2005S1 and Table\u2005S1 in theSupporting Information."},{"key":"e_1_2_6_16_2","unstructured":"\u00a0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2003.07.008"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/0021-9517(88)90246-1"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/b618573h"},{"key":"e_1_2_6_20_2","unstructured":"\u00a0"},{"key":"e_1_2_6_21_2","volume-title":"Fine Chemicals through Heterogeneous Catalysis","author":"Sheldon R. A.","year":"2001"},{"key":"e_1_2_6_22_2","volume-title":"Green Chemistry: Theory and Practice","author":"Anastas P. 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In contrast no co\u2010catalysts were necessary in the present Ru(OH)x\/Al2O3system; see:"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200500490"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja050770g"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/om990264y"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19990712)111:13\/14<2126::AID-ANGE2126>3.0.CO;2-T"},{"key":"e_1_2_6_39_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19990712)38:13\/14<1960::AID-ANIE1960>3.0.CO;2-4"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/a809236b"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9403695"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00058a059"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00013a015"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/C39910000473"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(91)80681-U"},{"key":"e_1_2_6_46_2","unstructured":"EXAFS analyses of supported ruthenium hydroxide catalysts have shown that the dispersion of the hydroxide species increases with an increase in the BET surface areas of the supports suggesting that the highly dispersed ruthenium hydroxide species exhibits high catalytic activity. Detailed studies are in progress."},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar9700163"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20011203)7:23<5052::AID-CHEM5052>3.0.CO;2-Z"},{"key":"e_1_2_6_49_2","unstructured":"\u03b1 \u03b2\u2010Unsaturated carbonyl compounds could be detected at the initial stage (conversion<20\u2009%) of the reduction of1\u2009a\u20104\u2009a 11\u2009a and13\u2009a but the amounts were very small (less than 1\u2009%)."},{"key":"e_1_2_6_50_2","unstructured":"\u00a0"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja043782v"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2003.12.002"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja035435b"},{"key":"e_1_2_6_54_2","unstructured":"Whereas it has been reported that \u03b3\u2010Al2O3pretreated at high temperature (at least 573\u2005K) can act as a catalyst for the MPV\u2010type reduction of carbonyl compounds the activity is very low; see:"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0166-9834(00)82455-0"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00427a022"},{"key":"e_1_2_6_57_2","unstructured":"It was confirmed by separate experiments that the kinetic isotope effect (kH\/kD) for the MPV\u2010type reduction of acetophenone in 2\u2010propanol and in 2\u2010deuterio\u20102\u2010propanol was 5.3."},{"key":"e_1_2_6_58_2","volume-title":"Purification of Laboratory Chemicals","year":"1988"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo971046m"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1039\/p29900001651"},{"key":"e_1_2_6_61_2","unstructured":"\u00a0"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1016\/0021-9517(87)90312-5"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0920-5861(96)00214-3"},{"key":"e_1_2_6_64_2","doi-asserted-by":"publisher","DOI":"10.1016\/0021-9517(92)90110-4"},{"key":"e_1_2_6_65_2","first-page":"82nd","author":"Williams G. 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