Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines.
Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines.
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DOI：
10.3762/bjoc.10.69
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发表时间：
2014
影响因子：
2.7
通讯作者：
Li G
中科院分区：
文献类型：
--
作者：
Xie JB;Luo J;Winn TR;Cordes DB;Li G
抗癌药物万珂的一种新的方法是通过进行不对称硼基化的亚胺锚定与手性N-膦基辅助。在整个7步合成中，特别是在亚胺的合成和不对称硼基化反应中，操作和后处理以简单和容易的方式进行，而无需任何柱色谱纯化，这定义差距（基团辅助纯化）化学概念。结果表明，不对称硼基化反应产物经正己烷洗涤后，可得到光学纯的异构体（dr > 99：1），脱保护后可回收手性N-膦基助剂。还研究了其他几种N-膦亚胺的不对称硼化反应。通过单晶X射线衍射分析证实了硼化产物的绝对构型。
A new approach to the anticancer drug Velcade was developed by performing asymmetric borylation of an imine anchored with a chiral N-phosphinyl auxiliary. Throughout the 7-step synthesis, especially in the imine’s synthesis and in the asymmetric borylation reactions, operations and work-up were conducted in simple and easy ways without any column chromatographic purification, which defines the GAP (group-assisted purification) chemistry concept. It was found that the optically pure isomer (dr > 99:1) can be readily obtained by washing the crude mixture of the asymmetric borylation reaction with hexane; the chiral N-phosphinyl auxiliary can be easily recovered after deprotection is finished. Several other N-phosphinylimines were also investigated for the asymmetric borylation reaction. The absolute configuration of the borylation product was confirmed by single crystal X-ray diffraction analysis.
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影响因子：
16.6
作者：
Ibrahem, Ismail;Breistein, Palle;Cordova, Armando
通讯作者：
Cordova, Armando
影响因子：
15
作者：
Lee Y;Hoveyda AH
通讯作者：
Hoveyda AH
DOI：
10.1021/jo400354r
发表时间：
2013-04-19
期刊：
The Journal of organic chemistry
影响因子：
--
作者：
Pindi S;Wu J;Li G
通讯作者：
Li G
影响因子：
5.2
作者：
Lauzon, Caroline;Charette, Andre B.
通讯作者：
Charette, Andre B.
影响因子：
3
作者：
Pindi, Suresh;Kaur, Parminder;Li, Guigen
通讯作者：
Li, Guigen