French Family Science Center, Duke University, Durham, North Carolina 27708-0346, USA.
J Am Chem Soc. 2009 Apr 22;131(15):5372-3. doi: 10.1021/ja9001162.
Reaction of 1-methyl-imidazolidin-2-one (1) with 1-octene (10 equiv) catalyzed by a 1:1 mixture of (2b)AuCl [2b = 2-di-tert-butylphosphino-1,1'-binaphthyl] and AgSbF(6) in dioxane at 100 degrees C for 24 h led to isolation of 1-methyl-3-(octan-2-yl)imidazolidin-2-one in 96% yield as a single regioisomer. A range of unactivated 1-alkenes and ethylene underwent gold(I)-catalyzed intermolecular hydroamination at or below 100 degrees C in excellent yield with high regioselectivity. Reaction of 1-alkenes with substituted imidazolidin-2-ones catalyzed by chiral bis(gold) phosphine complexes led to enantioselective intermolecular hydroamination with up to 78% ee.
1-甲基-2-咪唑啉酮(1)与 1-辛烯(10 当量)在二氧六环中,经(2b)AuCl [2b = 2-二叔丁基膦-1,1'-联萘]和 AgSbF(6)的 1:1 混合物催化,于 100°C 下反应 24 小时,得到了 96%收率的单一区域异构体 1-甲基-3-(辛-2-基)咪唑啉-2-酮。一系列未活化的 1-烯烃和乙烯在 100°C 或以下的温度下,经金(I)催化的分子间氨氢化反应,以优异的收率和高区域选择性进行。手性双(金)膦配合物催化取代的咪唑啉-2-酮与 1-烯烃的反应,导致对映选择性的分子间氨氢化反应,ee 值最高可达 78%。