Department of Chemistry, Stanford University, Stanford, California 94305-5080, United States.
Org Lett. 2012 Dec 21;14(24):6174-7. doi: 10.1021/ol302895f. Epub 2012 Dec 10.
A general, high yielding method for the synthesis of 1,2-diamine derivatives is described that capitalizes on selective, rhodium-catalyzed C-H insertion of hydroxylamine-based sulfamate esters. The resulting Troc-protected oxathiadiazinane heterocycles are easily modified and can be reduced under the mild action of NaI to afford differentially substituted diamine products. This technology offers a number of salient improvements over related C-H and π-bond amination tactics for diamine synthesis.
描述了一种通用的、高产率的 1,2-二胺衍生物的合成方法，该方法利用选择性的、铑催化的羟胺基磺酰胺酯的 C-H 插入反应。得到的 Troc 保护的氧杂噻二嗪烷杂环很容易被修饰，并且可以在温和的碘化钠作用下还原，得到不同取代的二胺产物。与相关的 C-H 和π键胺化策略相比，该技术在二胺合成方面具有许多显著的改进。
