Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C–H Bond Functionalization | Zendy

Apiwat Wangweerawong | Zendy; Robert G. Bergman | Zendy; Jonathan A. Ellman | Zendy

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Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C–H Bond Functionalization

Author(s) -

Apiwat Wangweerawong,

Robert G. Bergman,

Jonathan A. Ellman

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja5033452

Subject(s) - chemistry , imine , substituent , amine gas treating , reactivity (psychology) , surface modification , intermolecular force , catalysis , medicinal chemistry , rhodium , organic chemistry , stereochemistry , molecule , medicine , alternative medicine , pathology

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.

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