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

ABSTRACT: The systematic investigation of substrate-bound ?-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 ?-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

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

Kim Jinhee J Sim Mikyung M Kim Namhoon N Hong Sungwoo S

Chemical science 20150416 6

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. ...[more]

PMID: 29511524

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