Asymmetric C-H functionalization of cyclopropanes using an isoleucine-NH₂ bidentate directing group.

ABSTRACT: The systematic investigation of substrate-bound α-amino acid auxiliaries has resulted in catalytic asymmetric C-H functionalization of cyclopropanes enabled by amino acid amides as chiral bidentate directing groups. The use of an Ile-NH₂ auxiliary embedded in the substrate provided excellent levels of asymmetric induction (diastereomeric ratio of up to 72 : 1) in the Pd(ii)-catalyzed β-methylene C(sp³)-H bond activation of cyclopropanes and cross-coupling with aryl iodides.

SUBMITTER: Kim J 

PROVIDER: S-EPMC5659170 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature