Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry , University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry , University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
J Am Chem Soc. 2018 Apr 4;140(13):4508-4511. doi: 10.1021/jacs.8b01754. Epub 2018 Mar 27.
Carborane cage chirality is an outstanding issue of great interest as the icosahedral carboranes have wide applications in medicinal and materials chemistry. The synthesis of optically active carborane derivatives, whose chirality is associated with the substitution patterns on the polyhedron, will open new avenues to carborane chemistry. We report herein an efficient method to achieve chiral-at-cage arylation of o-carboranes with high regio- and enantioselectivities by a strategy of palladium-catalyzed asymmetric intramolecular B-H arylation and cyclization. This represents the first example of the enantioselective reaction on carboranes, providing an efficient way for the construction of chiral-at-cage compounds with new skeletons.
笼型碳硼烷的手性是一个非常有趣的突出问题，因为二十面体碳硼烷在药物和材料化学中有广泛的应用。具有与多面体取代模式相关的手性的光学活性碳硼烷衍生物的合成将为碳硼烷化学开辟新的途径。我们在此报告了一种通过钯催化的不对称分子内 B-H 芳基化和环化策略，以高区域和对映选择性实现邻位碳硼烷笼型芳基化的有效方法。这代表了碳硼烷对映选择性反应的第一个例子，为具有新骨架的笼型手性化合物的构建提供了一种有效的方法。
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