Enantioselective Synthesis of Chiral 3-Substituted Tetrahydroquinolines via a Pd-Catalyzed C-C Cleavage/C-C Coupling Sequence
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Updated: Oct 25, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Cheng-Yu Li1, Xiao-Jing Liu1, Zhen-Ting Mao1
1College of Chemical Engineering, State Key Laboratory of Advanced Separation Membrane Materials, Zhejiang University of Technology, ChaowangRoad #18, Hangzhou310014, China.
Abstract:
A palladium-catalyzed asymmetric synthesis of 3-substituted tetrahydroquinolines (THQs) through a C-C cleavage/C-C coupling sequence has been developed. By employing Pd(OAc)2/Josiphos L7 as the catalyst, an array of chiral tetrahydroquinolines bearing a C3-ketone pendant was afforded in good to excellent yields and enantioselectivities by using 3-(2-bromoaniline)-tethered cyclobutanols as substrates. Control experiments revealed that only cis-substrates were able to participate in the reaction. In addition, several synthetic transformations derived from the ketone moiety were carried out to demonstrate the practical utility of this protocol.
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