对映选择合成
化学
弗里德尔-克拉夫茨反应
烷基化
苯胺
有机催化
有机化学
组合化学
催化作用
立体化学
作者
Ruilin Zhang,Bo Liu,Kaixiong Qiu,Hongtao Li,Hui-Nan Zhang,Baochun Shen,Zhong‐Wen Sun
出处
期刊:Organic Letters
[American Chemical Society]
日期:2023-03-09
卷期号:25 (10): 1711-1716
被引量:8
标识
DOI:10.1021/acs.orglett.3c00370
摘要
Herein, we described a highly regio- and enantioselective Friedel–Crafts alkylation of aniline derivatives with in situ generated ortho-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.
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