Asymmetric C-H Functionalization of Cyclopropanes Using an Isoleucine-NH2 Bidentate Directing Group

Abstract

The systematic investigation of substrate-bound a-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 b-methylene C(sp3)–H bond activation of cyclopropanes and cross-coupling with aryl iodides.

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