Enantioselective ortho-C-H Addition of Aromatic Amines to Alkenes by Bulky Chiral Anilido-Oxazoline Scandium Complexes
Qianlin Sun, Xiangli Feng, Xintong Wang, Haowen Shi, Jianhong Su, Mingxuan Wang, Gen Luo（罗根）*, Xin Xu（徐信）*
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China
2Institutes of Physical Science and Information Technology, Anhui University, Hefei 230601, P. R. China
J. Am. Chem. Soc.2025, 147, 13658–13666
Abstract: The enantioselective C–H addition of anilines to alkenes represents an ideal protocol for the synthesis of chiral aromatic amines in terms of step- and atom-economy. However, this field remains predominantly unexplored. Herein, a series of newly designed bulky chiral anilido-oxazoline ligand precursors were synthesized, and the corresponding rare-earth metal alkyl complexes were obtained successfully. The resultant scandium complexes exhibit high regioselectivity for the ortho-C–H addition of tertiary anilines to unactivated alkenes, providing a wide range of chiral alkylated anilines in high yields (up to 98% yield) with excellent enantioselectivity (up to 98% ee). Moreover, the addition products can be easily converted into biorelevant derivatives and pharmacophore-containing skeletons.
Article information: //doi.org/10.1021/jacs.5c00986
