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Palladium(II)-catalyzed highly enantioselective C-H arylation of cyclopropylmethylamines.

ABSTRACT: 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.

SUBMITTER: Chan KS

PROVIDER: S-EPMC4433166 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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Palladium(II)-catalyzed highly enantioselective C-H arylation of cyclopropylmethylamines.

Chan Kelvin S L KS Fu Hai-Yan HY Yu Jin-Quan JQ

Journal of the American Chemical Society 20150127 5

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 ...[more]

PMID: 25581489

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