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Copper‐Catalyzed Enantioselective Hydroboration of 1,1‐Disubstituted Alkenes: Method Development, Applications and Mechanistic Studies
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2017-11-13 , DOI: 10.1002/ajoc.201700503
Lu Wen 1 , Fengchang Cheng 1 , Han Li 2 , Shuoqing Zhang 2 , Xin Hong 2 , Fanke Meng 1
Affiliation  

Cu‐catalyzed enantioselective Cu–B(pin) addition to 1,1‐disubstituted alkenes generating tertiary alkylcopper complexes that contain a quaternary stereogenic center, followed by the protonation of the complexes are presented. The resulting formal hydroboration products are formed in up to 98 % yield and 99:1 enantiomeric ratio. The C–B(pin) moiety can be converted to a variety of useful functional groups. The method is applied to the enantioselective formal synthesis of (R)‐ketoprofen. Detailed stereochemical models for enantioselective induction were elucidated through DFT calculations.

中文翻译:

1,1-二取代烯烃的铜催化对映选择性硼氢化:方法开发,应用和机理研究

铜催化的对映选择性Cu-B(pin)加成到1,1-二取代的烯烃上,生成叔烷基铜配合物,其中包含季位立体中心,然后使配合物质子化。形成的正式硼氢化产物的收率高达98%,对映体比率为99:1。C–B(pin)部分可以转化为各种有用的官能团。该方法适用于(R)-酮洛芬的对映选择性形式合成。通过DFT计算阐明了对映选择性诱导的详细立体化学模型。
更新日期:2017-11-13
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