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Asymmetric synthesis of ?-branched amines via Rh(III)-catalyzed C-H bond functionalization.

ABSTRACT: The first asymmetric intermolecular addition of non-acidic C-H bonds to imines is reported. The use of the activating N-perfluorobutanesulfinyl imine substituent is essential for achieving sufficient reactivity and provides outstanding diastereoselectivity (>98:2 dr). Straightforward removal of the sulfinyl group with HCl yields the highly enantiomerically enriched amine hydrochlorides.

SUBMITTER: Wangweerawong A

PROVIDER: S-EPMC4105057 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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Asymmetric synthesis of α-branched amines via Rh(III)-catalyzed C-H bond functionalization.

Wangweerawong Apiwat A Bergman Robert G RG Ellman Jonathan A JA

Journal of the American Chemical Society 20140605 24

The first asymmetric intermolecular addition of non-acidic C-H bonds to imines is reported. The use of the activating N-perfluorobutanesulfinyl imine substituent is essential for achieving sufficient reactivity and provides outstanding diastereoselectivity (>98:2 dr). Straightforward removal of the sulfinyl group with HCl yields the highly enantiomerically enriched amine hydrochlorides. ...[more]

PMID: 24901217

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