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The thermodynamically unstable ketone aldols undergo a facile retro\u2010aldolization to yield a presumed zirconium enolate in situ, which then undergoes the aldol\u2010Tishchenko reaction in typically high yields and with complete 1,3\u2010<jats:italic>anti<\/jats:italic> diastereocontrol. Evaluation of a broad range of metal alkoxides as catalysts and optimization of the reaction protocol led to a modified zirconium alkoxide catalyst with attenuated Lewis acidity and dichloromethane as solvent, which resulted in suppression of the undesired acyl migration to a large extent. Various ketone aldols have been prepared and subjected to the general process, giving rise to a broad range of differently substituted 1,3\u2010<jats:italic>anti<\/jats:italic>\u2010diol monoesters, which may be hydrolyzed to the corresponding 1,3\u2010<jats:italic>anti<\/jats:italic>\u2010diols.<\/jats:p>","DOI":"10.1002\/chem.200400951","type":"journal-article","created":{"date-parts":[[2005,3,15]],"date-time":"2005-03-15T08:46:47Z","timestamp":1110876407000},"page":"3010-3021","source":"Crossref","is-referenced-by-count":41,"title":["The Zirconium Alkoxide\u2010Catalyzed Aldol\u2010Tishchenko Reaction of Ketone Aldols"],"prefix":"10.1002","volume":"11","author":[{"given":"Christoph","family":"Schneider","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Markus","family":"Hansch","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Timo","family":"Weide","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2005,4,28]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01191a007"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01203a011"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.2174\/1385272033486224"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo972128d"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr950027e"},{"key":"e_1_2_6_7_2","unstructured":"\u00a0"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/C39910001016"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo971012e"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1996-4339"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2000-6247"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/00404-0399(50)0985L-"},{"key":"e_1_2_6_13_2","unstructured":"\u00a0"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1991-34728"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo981675b"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol990246c"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010202)113:3<621::AID-ANGE621>3.0.CO;2-2"},{"key":"e_1_2_6_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010202)40:3<601::AID-ANIE601>3.0.CO;2-W"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja047906f"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.08.134"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)00579-2"},{"key":"e_1_2_6_20_3","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(03)01191-8"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/b102941j"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2003-38741"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20011001)7:19<4066::AID-CHEM4066>3.0.CO;2-K"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9520002027"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9520004204"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja003033n"},{"key":"e_1_2_6_26_3","doi-asserted-by":"publisher","DOI":"10.1021\/ja015580u"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)88405-1"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1071\/CH9781737"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19310640911"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00173a071"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar960223n"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19911240543"}],"container-title":["Chemistry 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