{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,26]],"date-time":"2025-10-26T13:57:08Z","timestamp":1761487028178,"version":"build-2065373602"},"reference-count":49,"publisher":"Wiley","issue":"17","license":[{"start":{"date-parts":[[2003,8,22]],"date-time":"2003-08-22T00:00:00Z","timestamp":1061510400000},"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":[[2003,9,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A library of novel dipeptide\u2010analogue ligands based on the combination of <jats:italic>tert<\/jats:italic>\u2010butoxycarbonyl(<jats:italic>N<\/jats:italic>\u2010Boc)\u2010protected <jats:italic>\u03b1<\/jats:italic>\u2010amino acids and chiral vicinal amino alcohols were prepared. These highly modular ligands were combined with [{RuCl<jats:sub>2<\/jats:sub>(<jats:italic>p\u2010<\/jats:italic>cymene)}<jats:sub>2<\/jats:sub>] and the resulting metal complexes were screened as catalysts for the enantioselective reduction of acetophenone under transfer hydrogenation conditions using 2\u2010propanol as the hydrogen donor. Excellent enantioselectivity of 1\u2010phenylethanol (up to 98\u2009% <jats:italic>ee<\/jats:italic>) was achieved with several of the novel catalysts. Although most of the ligands contained two stereocenters, it was demonstrated that the absolute configuration of the product alcohol was determined by the configuration of the amino acid part of the ligand. Employing ligands based on <jats:sc>L<\/jats:sc>\u2010amino acids generated <jats:italic>S<\/jats:italic>\u2010configured products, and catalysts based on <jats:sc>D<\/jats:sc>\u2010amino acids favored the formation of the <jats:italic>R<\/jats:italic>\u2010configured alcohol. The combination <jats:italic>N<\/jats:italic>\u2010Boc\u2010<jats:sc>L<\/jats:sc>\u2010alanine and (<jats:italic>R<\/jats:italic>)\u2010phenylglycinol (<jats:bold>Boc\u2010<jats:sc>L<\/jats:sc>\u2010Ab<\/jats:bold>) or its enantiomer (<jats:italic>N<\/jats:italic>\u2010Boc\u2010<jats:sc>D<\/jats:sc>\u2010alanine and (<jats:italic>S<\/jats:italic>)\u2010phenylglycinol, <jats:bold>Boc\u2010<jats:sc>D<\/jats:sc>\u2010Aa<\/jats:bold>) proved to be the best ligands for the reduction process. Transfer hydrogenation of a number of aryl alkyl ketones were evaluated and excellent enantioselectivity, up to 96\u2009% <jats:italic>ee<\/jats:italic>, was obtained.<\/jats:p>","DOI":"10.1002\/chem.200304900","type":"journal-article","created":{"date-parts":[[2003,9,2]],"date-time":"2003-09-02T15:37:14Z","timestamp":1062517034000},"page":"4031-4045","source":"Crossref","is-referenced-by-count":79,"title":["Employing the Structural Diversity of Nature: Development of Modular Dipeptide\u2010Analogue Ligands for Ruthenium\u2010Catalyzed Enantioselective Transfer Hydrogenation of Ketones"],"prefix":"10.1002","volume":"9","author":[{"given":"Isidro M.","family":"Pastor","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Patrik","family":"V\u00e4stil\u00e4","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hans","family":"Adolfsson","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2003,8,22]]},"reference":[{"key":"e_1_2_6_1_2","first-page":"199","volume-title":"Comprehensive Asymmetric Catalysis I","author":"Ohkuma T.","year":"1999"},{"key":"e_1_2_6_2_2","unstructured":"For reviews see:"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar9502341"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(99)00216-5"},{"key":"e_1_2_6_5_2","unstructured":"\u00a0"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00133a037"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja954126l"},{"key":"e_1_2_6_8_2","unstructured":"\u00a0"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo972082o"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo991914a"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20010401)7:7<1431::AID-CHEM1431>3.0.CO;2-L"},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo970405a"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1169(99)00062-X"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/b108538g"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/cc9960000233"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/B206471E"},{"key":"e_1_2_6_18_2","unstructured":"\u00a0"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1998.491"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/aoc.216"},{"key":"e_1_2_6_21_2","unstructured":"\u00a0"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3765(19990503)5:5<1544::AID-CHEM1544>3.0.CO;2-T"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(99)00433-7"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/1615-4169(200207)344:5<499::AID-ADSC499>3.0.CO;2-R"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/om010644v"},{"key":"e_1_2_6_26_2","unstructured":"\u00a0"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)00914-5"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/b106130p"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)02132-3"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)00087-4"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9613491"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo990213a"},{"key":"e_1_2_6_33_2","unstructured":"Please observe that only one of two possible diastereomers of the postulated ruthenium complexes is depicted in Schemes 4 and 5."},{"key":"e_1_2_6_34_2","unstructured":"In previous reports on (\u03b76\u2010arene)RuIIcomplexes with peptide ligands coordination of the amide nitrogen was demonstrated. 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