Massive parallel catalyst screening: Toward asymmetric MCRs
Massive parallel catalyst screening: Toward asymmetric MCRs
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DOI：
10.1021/ol035010u
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发表时间：
2003-10-30
期刊：
影响因子：
5.2
通讯作者：
Domling, A
中科院分区：
文献类型：
--
作者：
Kusebauch, U;Beck, B;Domling, A
[图解]已筛选了数百种刘易斯酸/配体组合，用于Passerini多组分反应中的立体化学诱导。在几个实施例中，发现四异丙醇钛和（4S，5S）-4，5-双（二苯基羟甲基）-2，2-二甲基二氧戊环的组合产生32%至42%的对映体过量。一个实例的绝对立体诱导是通过化学和X射线晶体学测定的。这包括第一个不对称Passerini反应和通过手性刘易斯酸在基于异氰化物的多组分反应中立体化学诱导的第一个实例。
[GRAPHIC]Hundreds of Lewis acid/ligand combinations have been screened for stereochemical induction in the Passerini multicomponent reaction. The combination of titan tetraisopropylate and (4S,5S)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyidioxolane was found to give enantiomeric excesses between 32% and 42% in several examples. The absolute stereo induction of one example was determined chemically and by means of X-ray crystallography. This comprises the first asymmetric Passerini reaction and the first example of a stereochernical induction in an isocyanide based multicomponent reaction by a chiral Lewis acid.