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Li ZY, Lakmal HHC, Qian X, et al. Ruthenium-Catalyzed Enantioselective C-H Functionalization: A Practical Access to Optically Active Indoline Derivatives. J Am Chem Soc. 2019;141(40):15730-15736doi: 10.1021/jacs.9b07251.
Li, Z. Y., Lakmal, H. H. C., Qian, X., Zhu, Z., Donnadieu, B., McClain, S. J., Xu, X., & Cui, X. (2019). Ruthenium-Catalyzed Enantioselective C-H Functionalization: A Practical Access to Optically Active Indoline Derivatives. Journal of the American Chemical Society, 141(40), 15730-15736. https://doi.org/10.1021/jacs.9b07251
Li, Zhong-Yuan, et al. "Ruthenium-Catalyzed Enantioselective C-H Functionalization: A Practical Access to Optically Active Indoline Derivatives." Journal of the American Chemical Society vol. 141,40 (2019): 15730-15736. doi: https://doi.org/10.1021/jacs.9b07251
Li ZY, Lakmal HHC, Qian X, Zhu Z, Donnadieu B, McClain SJ, Xu X, Cui X. Ruthenium-Catalyzed Enantioselective C-H Functionalization: A Practical Access to Optically Active Indoline Derivatives. J Am Chem Soc. 2019 Oct 09;141(40):15730-15736. doi: 10.1021/jacs.9b07251. Epub 2019 Sep 26. PMID: 31536341.
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J Am Chem Soc. 2019 Oct 09;141(40):15730-15736. doi: 10.1021/jacs.9b07251. Epub 2019 Sep 26.

Ruthenium-Catalyzed Enantioselective C-H Functionalization: A Practical Access to Optically Active Indoline Derivatives.

Journal of the American Chemical Society

Zhong-Yuan Li, Hetti Handi Chaminda Lakmal, Xiaolin Qian, Zhenyu Zhu, Bruno Donnadieu, Sarah J McClain, Xue Xu, Xin Cui

Affiliations

  1. Department of Chemistry , Mississippi State University , Mississippi State , Mississippi 39762 , United States.

PMID: 31536341 DOI: 10.1021/jacs.9b07251

Abstract

Ru(II)-catalyzed enantioselective C-H activation/hydroarylation has been developed for the first time, allowing for highly enantioselective synthesis of indoline derivatives via catalytic C-H activation. Commercially available Ru(II) arene complexes and chiral α-methylamines were employed as highly enantioselective catalysts. Based on a sterically rigidified chiral transient directing group, multisubstituted indolines were produced in up to 92% yield with 96% ee. Further transformation of the resulting 4-formylindoline enables access to an optically active tricyclic compound that is of potential biological and pharmaceutical interest.

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