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首页> 外文期刊>Chemistry: A European journal >Asymmetric Allylation of Ketones and Subsequent Tandem Reactions Catalyzed by a Novel Polymer-Supported Titanium– BINOLate Complex**
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Asymmetric Allylation of Ketones and Subsequent Tandem Reactions Catalyzed by a Novel Polymer-Supported Titanium– BINOLate Complex**

机译：新型聚合物支撑的钛-双酚盐配合物催化的酮的不对称烯丙基化及随后的串联反应**

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摘要

By using a novel, simple, and convenient synthetic route, enantiopure 6-ethynyl-BINOL (BINOL=1,1-binaphthol) was synthesized and anchored to an azidomethylpolystyrene resin through a copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction. The polystyrene (PS)-supported BINOL ligand was converted into its diisopropoxytitanium derivative in situ and used as a heterogeneous catalyst in the asymmetric allylation of ketones. The catalyst showed good activity and excellent enantioselectivity, typically matching the results obtained in the corresponding homogeneous reaction. The allylation reaction mixture could be submitted to epoxidation by simple treatment with tert-butyl hydroperoxide (TBHP), and the tandem asymmetric allylation epoxidation process led to a highly enantioenriched epoxy alcohol with two adjacent quaternary centers as a single diastereomer. A tandem asymmetric allylation/Pauson–Khand reaction was also performed, involving simple treatment of the allylation reaction mixture with Co_2(CO)_8/N-methyl morpholine N-oxide. This cascade process resulted in the formation of two diastereomeric tricyclic enones in high yields and enantioselectivities.
机译：通过使用新颖，简单和方便的合成途径，合成了对映纯6-乙炔基-BINOL（BINOL = 1,1-binaphthol），并通过铜催化的炔-叠氮化物环加成（CuAAC）反应固定在叠氮基甲基聚苯乙烯树脂上。将聚苯乙烯（PS）负载的BINOL配体原位转化为其二异丙氧基钛衍生物，并在酮的不对称烯丙基化反应中用作多相催化剂。该催化剂显示出良好的活性和优异的对映选择性，通常与在相应的均相反应中获得的结果相匹配。烯丙基化反应混合物可以通过用叔丁基氢过氧化物（TBHP）进行简单处理而进行环氧化，而串联不对称烯丙基化环氧化过程导致高度对映体富集的环氧醇具有两个相邻的季铵中心作为单个非对映异构体。还进行了串联不对称烯丙基化/ Pauson-Khand反应，包括用Co_2（CO）_8 / N-甲基吗啉N-氧化物对烯丙基化反应混合物进行简单处理。该级联过程以高收率和对映选择性形成了两个非对映异构的三环烯酮。

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