Evidence for a boroxinate based Brønsted acid derivative of VAPOL as the active catalyst in the catalytic asymmetric aziridination reaction.
Evidence for a boroxinate based Brønsted acid derivative of VAPOL as the active catalyst in the catalytic asymmetric aziridination reaction.
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DOI：
10.1021/ja904589k
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发表时间：
2009-11-04
影响因子：
15
通讯作者：
Wulff, William D.
中科院分区：
文献类型：
--
作者：
Hu, Gang;Huang, Li;Huang, Rui H.;Wulff, William D.
研究了亚胺与重氮乙酸乙酯的不对称催化氮丙啶化反应（AZ反应）中活性催化剂的结构。有证据表明，活性催化剂含有一个环硼氧烷环中的三个硼原子之一是螺稠合的VAPOL配体的两个苯酚基团。11 B和1H NMR证据支持环硼氧烷结构B，其中的反式环硼氧烷是质子化形式的亚胺。硼氧酸盐结构也由VAPOL硼氧酸盐的两种固态结构支撑，其中gegen阳离子是四甲基铵和4-二甲基氨基吡啶鎓。
Studies are described that were designed to determine the structure of the active catalyst in the asymmetric catalytic aziridination of imines with ethyl diazoacetate (AZ reaction). Evidence suggests that the active catalyst contains a boroxine ring in which one of the three boron atoms is spiro-fused with the two phenol groups of the VAPOL ligand.11B and1H NMR evidence supports the boroxinate structure B in which the counterion to the boroxinate is the protonated form of the imine. The boroxinate structure is also supported by two solid state structures of a VAPOL boroxinate in which the gegen cation is tetramethyl ammonium and 4-dimethylaminopyridinium.
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