Synthesis of dihydroquinolinones
A Rh/Pd/Cu catalyst system led to an efficient one-pot synthesis of dihydroquinolinones without any intermediate workup. The conjugate-addition/amidation/amidation reaction sequence is highly modular, divergent, and practical.
L. Zhang, L. Sonaglia, J. Stacey, M. Lautens, Org. Lett., 2013, 15, 2128-2131.
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.
J.-H. Jin, H. Wang, Z.-T. Yang, W.-L. Yang, W. Tang, W.-P. Deng, Org. Lett., 2018, 20, 104-107.
In an asymmetric [4+2] cycloaddition of vinyl benzoxazinanones with a variety of ketene intermediates via sequential visible-light photoactivation and palladium catalysis, the traceless and transient generation of ketenes from α-diazoketones through visible-light-induced Wolff rearrangement is important for the success of the palladium catalysis.
M.-M. Li, Y. Wei, J. Liu, H.-W. Chen, L.-Q. Lu, W.-J. Xiao, J. Am. Chem. Soc., 2017, 139, 14707-14713.