{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2023,9,13]],"date-time":"2023-09-13T20:57:55Z","timestamp":1694638675088},"reference-count":0,"publisher":"Swiss Chemical Society","issue":"1-2","license":[{"start":{"date-parts":[[2010,2,26]],"date-time":"2010-02-26T00:00:00Z","timestamp":1267142400000},"content-version":"unspecified","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chimia"],"abstract":"<jats:p>\n        The first highly enantioselective, catalytic asymmetric synthesis of di-des-methylsibutramine 3 is described. Dienamide 10, prepared by acetic acid anhydride quenching of the condensation product of nitrile 4 with a methallyl magnesium chloride, proved to be an\n excellent substrate for ruthenium-catalyzed asymmetric hydrogenation with atropisomeric diphosphine ligands. Hydrogenation with a ruthenium\/(R)- MeOBiPheP catalyst at S\/C = 500, gave the chiral amide (R)-9 in 98.5% ee in almost quantitative yield. After acidic amide\n hydrolysis the desired amine (R)-3 was obtained without erosion of enantioselectivity. It is anticipated that the overall process will be amenable to large-scale production.\n      <\/jats:p>","DOI":"10.2533\/chimia.2010.59","type":"journal-article","created":{"date-parts":[[2010,3,10]],"date-time":"2010-03-10T04:05:33Z","timestamp":1268193933000},"page":"59","source":"Crossref","is-referenced-by-count":3,"title":["Highly Enantioselective Catalytic Asymmetric Synthesis of a (R)-Sibutramin Precursor"],"prefix":"10.2533","volume":"64","author":[{"given":"Ulrich","family":"Berens","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andreas","family":"Hafner","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Oliver","family":"Dosenbach","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tanja","family":"Tritschler","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Franz","family":"Schwarzenbach","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hans-J\u00f6rg","family":"Kirner","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christophe","family":"Malan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Oanh","family":"Mai-Huynh","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1442","published-online":{"date-parts":[[2010,2,26]]},"container-title":["CHIMIA"],"original-title":[],"link":[{"URL":"https:\/\/chimia.ch\/chimia\/article\/download\/4800\/4090","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chimia.ch\/chimia\/article\/download\/4800\/4090","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,1,28]],"date-time":"2022-01-28T09:49:48Z","timestamp":1643363388000},"score":1,"resource":{"primary":{"URL":"https:\/\/chimia.ch\/chimia\/article\/view\/4800"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,2,26]]},"references-count":0,"journal-issue":{"issue":"1-2","published-online":{"date-parts":[[2010,2,1]]}},"URL":"https:\/\/doi.org\/10.2533\/chimia.2010.59","relation":{},"ISSN":["2673-2424","0009-4293"],"issn-type":[{"value":"2673-2424","type":"electronic"},{"value":"0009-4293","type":"print"}],"subject":[],"published":{"date-parts":[[2010,2,26]]}}}