Enantioselective and Diastereoselective C–H Alkylation of Benzamides: Synergized Axial and Central Chirality via a Single Stereodetermining Step

In this report, distally disposed
axial and central chirality has
been installed in a synergistic fashion via rhodium-catalyzed C–H
alkylation of benzamides using N-arylmaleimide as
the alkylating reagent, in which the enantio- and diastereo-determining
steps are merged into a single one. The coupling system features mild
reaction conditions, broad substrate scope, and excellent enantio-
and diastereoselectivity. The chiral induction has been enabled by
judicious choice of a chiral rhodium cyclopentadienyl catalyst that
serves to control both the orientation of the olefin unit and the
prochiral C–N bond.