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Significance: The asymmetric enantioselective arylation of enecarbamates catalyzed by a chiral Brønsted acid is reported. An axially chiral dicarboxylic acid (1) catalyzes the reaction of quinone imine ketals 2 with enecarbamates 3 to give αamino-β-aryl ethers 4 in good yields and enantioselectivities. The products could be transformed into various useful chiral building blocks. Comment: It is notable that opposite enantiomers of the products are obtained by changing from Zto E-enecarbamates. The authors propose that the isomeric enecarbamates approach the quinone imine ketals 2 from the same prochiral face, and that diastereomeric intermediates are generated that lead to the opposite enantiomers after aromatization. N Boc H 2 R1 = H, Alk, Cl, Ph, OMe R2 = Boc, Bz, Ac, Cbz

Enantioselective Arylation of Enecarbamates with Quinone Imine Ketals