Kinetic Resolution of β-Alkyl Phenylethylamine Derivatives through Palladium-Catalyzed, Nosylamide-Directed C−H Olefination
Zeng Zhao,
Jinxin Wang,
Zhiteng Du,
Yuzhu Li,
Qingyan Sun,
Huizi Jin
Affiliations
Zeng Zhao
School of Pharmacy, Shanghai jiaotong University, Shanghai 200240, China
Jinxin Wang
School of Pharmacy, Second Military Medical University, Shanghai 200433, China
Zhiteng Du
Department of Pharmacy, Wenzhou Medical University, Wenzhou 325035, China
Yuzhu Li
School of Pharmacy, Shanghai jiaotong University, Shanghai 200240, China
Qingyan Sun
State Key Laboratory of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai 201203, China
Huizi Jin
School of Pharmacy, Shanghai jiaotong University, Shanghai 200240, China
Palladium-catalyzed C-H activation reactions have attracted the attention of organic researchers due to their unique high selectivity, broad functional group tolerance, and high efficiency, and they are widely used in natural products and asymmetric synthesis. Here, we report an example of enantioselective C-H alkenylation between β-alkyl phenylethylamine compounds and styrenes with Boc-L-lle-OH as the ligand and nosylamide as the directing group. This reaction is applicable to styrene containing various electron-deficient and electron-donating substitutions and may be utilized for the synthesis of benzoazepine compounds.
