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Asymmetric C-H functionalization of cyclopropanes using an isoleucine-NH2 bidentate directing group
Jinhee Kim1,2, Mikyung Sim1,2, Namhoon Kim1,2
1Department of Chemistry , Korea Advanced Institute of Science and Technology , Daejeon , 305-701 , Korea.
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.
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