Enantioselective Synthesis of Di- and Tri-Arylated All-Carbon Quaternary Stereocenters via Copper-Catalyzed Allylic Arylations with Organolithium Compounds
Enantioselective Synthesis of Di- and Tri-Arylated All-Carbon Quaternary Stereocenters via Copper-Catalyzed Allylic Arylations with Organolithium Compounds
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DOI：
10.1021/acscatal.6b01681
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发表时间：
2016-10-01
期刊：
影响因子：
12.9
通讯作者：
Feringa, Ben L.
中科院分区：
文献类型：
--
作者：
Guduguntla, Sureshbabu;Gualtierotti, Jean-Baptiste;Feringa, Ben L.
通过与芳基有机锂化合物的不对称烯丙基芳基化反应（AAAr），证明了铜(I)/ n杂环碳（NHC）催化合成二芳基化和三芳基化全碳季立体中心的高度对映选择性。在铜/NHC催化剂的存在下，使用容易获得或容易获得的芳基有机锂试剂与三取代的溴结合，可以得到重要的二芳基和三芳基化的全碳立体中心，收率高，对映选择性好。该方法可以在起始的烯丙基溴中使用广泛的烷基和取代芳基，包括不太常见的联芳基部分，与各种有机锂试剂结合使用，可以以操作简单有效的方式提供广泛的产品。
The highly enantioselective copper(I)/N-heterocyclic carbene (NHC) catalyzed synthesis of di- and triarylated all-carbon quaternary stereocenters via asymmetric allylic arylation (AAAr) with aryl organolithium compounds is demonstrated. The use of readily available or easily accessible aryl organolithium reagents in combination with trisubstituted ally) bromides, in the presence of a copper/NHC catalyst, affords important di- and triarylated all-carbon quaternary stereocenters in good yields and enantioselectivities. This method tolerates a wide range of alkyl and substituted aryl groups in the starting allyl bromides, including less common biaryl moieties, which, in combination with diverse organolithium reagents, delivers a broad scope of products in an operationally straightforward and efficient manner.