Copper(I)-Catalyzed Enantioselective Nucleophilic Borylation of Aldehydes: An Efficient Route to Enantiomerically Enriched α-Alkoxyorganoboronate Esters
Copper(I)-Catalyzed Enantioselective Nucleophilic Borylation of Aldehydes: An Efficient Route to Enantiomerically Enriched α-Alkoxyorganoboronate Esters
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DOI：
10.1021/ja511247z
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发表时间：
2015-01-14
影响因子：
15
通讯作者：
Ito, Hajime
中科院分区：
文献类型：
--
作者：
Kubota, Koji;Yamamoto, Eiji;Ito, Hajime
首次实现了C-O双键的催化不对称亲核硼化反应。在Cu（I）/DTBM-SEGPHOS复合催化剂存在下，以甲醇为质子源，一系列醛与二硼试剂反应，合成了具有光学活性的α-烷氧基有机硼酸酯。此外，产物可以容易地通过涉及立体C-B键的立体特异性C-C键形成反应转化为相应的官能化手性醇衍生物。
The first catalytic enantioselective nucleophilic borylation of a C-O double bond has been achieved. A series of aldehydes reacted with a diboron reagent in the presence of a copper(I)/DTBM-SEGPHOS complex catalyst using MeOH as a proton source to give the corresponding optically active a-alkoxyorganoboronate esters with excellent enantioselectivities. Furthermore, the products could be readily converted to the corresponding functionalized chiral alcohol derivatives through stereospecific C-C bond forming reactions involving the stereogenic C-B bond.