Asymmetric Synthesis of 3,4-Dihydroquinolin-2-ones via a Stereoselective Palladium-Catalyzed Decarboxylative [4 + 2]-Cycloaddition
Jing-Hai Jin, Hao Wang, Zhong-Tao Yang, Wu-Lin Yang, Wenjun Tang* and Wei-Ping Deng*
*School of Pharmacy and Shanghai Key Laboratory of New Drug
Design, East China University of Science and Technology, 130 Meilong Road,
Shanghai 200237, China, Email: weiping_deng
ecust.edu.cn,
tangwenjunsioc.ac.cn
J.-H. Jin, H. Wang, Z.-T. Yang, W.-L. Yang, W. Tang, W.-P. Deng, Org. Lett., 2018, 20, 104-107.
DOI: 10.1021/acs.orglett.7b03467
see article for more reactions
Abstract
The P-chiral monophosphorus ligand BI-DIME enables an efficient, palladium-catalyzed, decarboxylative [4 + 2]-cycloaddition of 4-vinyl benzoxazinanones with carboxylic acids to provide structurally diverse 3,4-dihydroquinolin-2-ones bearing two contiguous stereogenic centers in good yields with very good stereoselectivities.
see article for more examples
proposed mechanism
Key Words
ID: J54-Y2018
