Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000, China.
College of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, China.
J Org Chem. 2023 Mar 3;88(5):2841-2850. doi: 10.1021/acs.joc.2c02518. Epub 2023 Feb 22.
We demonstrated here an efficient synthetic method of carbazole derivatives from readily available -arylnaphthalen-2-amines and quinone esters catalyzed by Brønsted acid. With this strategy, a series of carbazole derivatives were obtained in good to excellent yields (76 to >99) under mild conditions. Large scale reaction illustrated the synthetic utility of this protocol. Meanwhile, a series of C-N axially chiral carbazole derivatives were also constructed in moderate to good yields (36-89% yield) with moderate to excellent atroposelectivities (44-94% ee) by using chiral phosphoric acid as a catalyst, which provides a novel strategy for the atroposelective construction of C-N axially chiral compounds and a new member of the C-N atropisomers.
我们在此展示了一种高效的咔唑衍生物的合成方法，该方法由易得的芳基萘-2-胺和醌酯在布朗斯台德酸催化下合成。采用该策略，在温和条件下以良好至优异的收率（76%至>99%）得到了一系列咔唑衍生物。放大反应表明了该方案的合成实用性。同时，使用手性磷酸作为催化剂，通过该方法还以中等至良好的收率（36-89%）构建了一系列 C-N 轴手性咔唑衍生物，对映选择性适中至优异（44-94%ee），为 C-N 轴手性化合物的对映选择性构建和 C-N 对映异构体提供了一种新策略。
