Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto, 606-8502, Japan.
Chem Asian J. 2011 Feb 1;6(2):607-13. doi: 10.1002/asia.201000604. Epub 2010 Nov 10.
The acid-catalyzed reaction of diazoacetates and aldimines (Brookhart-Templeton aziridination) is now recognized as a reliable method to provide enantiomerically enriched disubstituted aziridines, thus owing to the development of asymmetric catalysis. However, the extension of this method to prepare trisubstituted aziridines has not been explored to date, even for racemic products. In this context, and considering their synthetic importance and lack of alternative direct synthetic methods, we recently launched a program to realize this unmet challenge. Herein, we report a detailed study, which led to the establishment of a highly stereoselective synthesis for various trisubstituted aziridines, building on the use of N-α-diazoacyl camphorsultams as a key component.
氮宾与亚胺的酸催化反应（Brookhart-Templeton 氮丙啶化）现在被认为是提供对映体富集的二取代氮丙啶的可靠方法，这要归功于不对称催化的发展。然而，迄今为止，该方法尚未扩展到制备三取代氮丙啶，即使是外消旋产物。在这种情况下，考虑到它们的合成重要性和缺乏替代的直接合成方法，我们最近启动了一个项目来应对这一尚未满足的挑战。在这里，我们报告了一项详细的研究，该研究建立了一种使用 N-α-重氮酰基樟脑磺酰胺作为关键组分的各种三取代氮丙啶的高立体选择性合成方法。
