School of Forensic Medicine, Kunming Medical University, Kunming, Yunnan 650500, P. R. China.
School of Pharmaceutical Science & Yunnan Key Laboratory of Pharmacology for Natural Products, Kunming Medical University, Kunming, Yunnan 650500, P. R. China.
Org Lett. 2023 Mar 17;25(10):1711-1716. doi: 10.1021/acs.orglett.3c00370. Epub 2023 Mar 9.
Herein, we described a highly regio- and enantioselective Friedel-Crafts alkylation of aniline derivatives with generated -quinone methides enabled by chiral phosphoric acid, furnishing a wide range of enantioenriched triarylmethanes bearing three similar benzene rings in high yields (up to 98%) with excellent stereoselectivities (up to 98% ee). Furthermore, the large-scale reactions and diversified transformations of product demonstrate the practicality of the protocol. Density functional theory calculations elucidate the origin of the enantioselectivity.
在此，我们描述了手性磷酸促进的 生成的 -醌甲醚与苯胺衍生物的高区域和对映选择性 Friedel-Crafts 烷基化反应，以高产率（高达 98%）和优异的立体选择性（高达 98%ee）提供了广泛的含有三个相似苯环的对映体富集的三芳基甲烷。此外，产物的大规模反应和多样化转化证明了该方案的实用性。密度泛函理论计算阐明了对映选择性的起源。
