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J Am Chem Soc. 2014 Jun 18;136(24):8520-3. doi: 10.1021/ja5033452. Epub 2014 Jun 5.

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

Author information

1
Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.

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.

PMID:
24901217
PMCID:
PMC4105057
DOI:
10.1021/ja5033452
[Indexed for MEDLINE]
Free PMC Article

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