Axially Chiral Dicarboxylic Acid Catalyzed Activation of Quinone Imine Ketals: Enantioselective Arylation of Enecarbamates

by Takuya Hashimoto, Hiroki Nakatsu, Yuka Takiguchi and Keiji Maruoka

The synthetic utility of quinone imine ketals in the context of asymmetric catalysis was disclosed for the first time. By expanding the utility of chiral Brønsted acid catalysis to the electrophilic activation of quinone imine ketals, we succeeded in the development of highly enantioselective arylation of encarbamates to give α-amino-β-aryl ethers wherein quinone imine ketals act as functionalized aromatic ring surrogate. Further transformations of the products were also examined to establish procedures to provide chiral β-aryl amines and α-aryl esters.

Journal of the American Chemical Society

Article first published online: 22 OCT 2013

DOI: 10.1021/ja407501h