Asymmetric carbolithiation of conjugated enynes: a flow microreactor enables the use of configurationally unstable intermediates before they epimerize.

Asymmetric carbolithiation of conjugated enynes: a flow microreactor enables the use of configurationally unstable intermediates before they epimerize.
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DOI:
10.1021/ja110898s
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发表时间:
2011-02
影响因子:
15
通讯作者:
Yutaka Tomida;A. Nagaki;J. Yoshida
Yutaka Tomida;A. Nagaki;J. Yoshida
中科院分区:
化学1区
文献类型:
--
作者:
Yutaka Tomida;A. Nagaki;J. Yoshida

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我们发现,流动微反应器系统能够产生构型不稳定的手性有机锂中间体,并允许在电泳体异构化之前将其用于与电泳体的反应。在该方法的基础上,实现了共轭烯炔类化合物的对映体选择性碳化,然后与亲电试剂反应得到富含对映体的手性联烯类化合物。
We found that a flow microreactor system enables the generation of a configurationally unstable chiral organolithium intermediate and allows for its use in a reaction with an electrophile before it epimerizes. Based on this method, the enantioselective carbolithiation of conjugated enynes followed by the reaction with electrophiles was accomplished to obtain enantioenriched chiral allenes.