从手性三唑亚基卡宾衍生出的 Breslow 中间体的可分离类似物。
Isolable analogues of the Breslow intermediate derived from chiral triazolylidene carbenes.
机构信息
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
出版信息
J Am Chem Soc. 2012 Apr 11;134(14):6143-5. doi: 10.1021/ja302031v. Epub 2012 Mar 28.
Abstract
Since Breslow's initial report on the thiamine mode of action, the study of catalytic acyl carbanion processes has been an area of immense interest. With the advent of azolylidene catalysis, a plethora of reactivtiy has been harnessed, but the crucial nucleophilic intermediate proposed by Breslow had never been isolated or fully characterized. Herein, we report the isolation and full characterization of nitrogen analogues of the Breslow intermediate. Both stable and catalytically relevant, these species provide a model system for the study of acyl carbanion and homoenolate processes catalyzed by triazolylidene carbenes.
摘要
自 Breslow 最初报告硫胺素作用模式以来，催化酰基碳负离子过程的研究一直是一个极其感兴趣的领域。随着唑啉催化的出现，已经利用了大量的反应性，但 Breslow 提出的关键亲核中间体从未被分离或完全表征。在此，我们报告了 Breslow 中间体的氮类似物的分离和全表征。这些物种既稳定又与催化相关，为三唑啉烯碳烯催化的酰基碳负离子和偕烯醇化物过程的研究提供了模型体系。
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