An anionic nucleophilic catalyst system for the diastereoselective synthesis of trans-beta-lactams.
An anionic nucleophilic catalyst system for the diastereoselective synthesis of trans-beta-lactams.
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DOI：
10.1021/ol0511070
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发表时间：
2005-07
期刊：
影响因子：
5.2
通讯作者：
A. Weatherwax;Ciby J. Abraham;T. Lectka
中科院分区：
文献类型：
--
作者：
A. Weatherwax;Ciby J. Abraham;T. Lectka
反式二取代β-内酰胺在许多药物应用中显示出越来越多的实用性和突出性，使其不对称合成成为化学家的一个有吸引力的目标。我们介绍了一种阴离子，亲核催化剂系统，提供了一个有效的，非对映选择性路线，反式-二取代β-内酰胺，补充我们以前描述的催化方法，用于产生相应的顺式非对映异构体。这种催化的“转换机制”过程允许β-内酰胺的立体选择性合成的灵活性，根据需要从相同的底物产生顺式或反式产物。[反应：见正文]
Trans-disubstituted beta-lactams show increasing utility and prominence in numerous pharmaceutical applications, making their asymmetric synthesis an attractive goal for chemists. We introduce an anionic, nucleophilic catalyst system that provides an efficient, diastereoselective route to trans-disubstituted beta-lactams, a complement to our previously described catalytic methodology for generating the corresponding cis diastereomers. This catalytic, "switch mechanism" process allows for flexibility in the stereoselective synthesis of beta-lactams, producing either cis or trans products as desired from the same substrates. [reaction: see text]