Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides
Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides
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DOI：
10.1039/c8cc09523j
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发表时间：
2019-01-25
影响因子：
4.9
通讯作者：
Nakamura, Masaharu
中科院分区：
文献类型：
--
作者：
Iwamoto, Takahiro;Okuzono, Chiemi;Nakamura, Masaharu
首次实现了铁催化的Suzuki-Miyaura偶联反应。在催化量的FeCl2和(R，R)-QuinoxP*存在下，芳基硼酸锂与溴丙酸叔丁酯以对映体收敛的方式发生交叉偶联，从而可以方便地获得各种光学活性的芳基丙酸，包括几种具有商业价值的非甾体抗炎药(NSAID)。(R，R)-QuinoxP*与产生外消旋产物的类似的P-手性配体相比，能够特异性地诱导手性，突出了在目前的不对称交叉偶联体系中反金属化的关键重要性。
The first iron-catalysed enantioselective Suzuki-Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl2 and (R,R)-QuinoxP*, lithium arylborates are cross-coupled with tert-butyl -bromopropionate in an enantioconvergent manner, enabling facile access to various optically active -arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. (R,R)-QuinoxP* is specifically able to induce chirality when compared to analogous P-chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system.