Palladium(II)-Catalyzed Highly Enantioselective C--H Arylation of Cyclopropylmethylamines.

C--H arylation via a Pd(II)/Pd(IV) catalytic cycle has been one of the most extensively studied C--H activation reactions since the 1990s. Despite the rapid development of this reaction in the past two decades, an enantioselective version has not been reported to date. Herein, we report a Pd(II)-catalyzed highly enantioselective (up to 99.5% ee) arylation of cyclopropyl C--H bonds with aryl iodides using mono-N-protected amino acid (MPAA) ligands, providing a new route for the preparation of chiral cis-aryl-cyclopropylmethylamines. The enantiocontrol is also shown to override the diastereoselectivity of chiral substrates. [ABSTRACT FROM AUTHOR]