Simple Branched Sulfur–Olefins as Chiral Ligands for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Highly Enantioselective Construction of Tetrasubstituted Carbon Stereocenters

New, simple, sulfinamide-based branched olefin ligands have been developed and successfully used in Rh-catalyzed asymmetric arylations of cyclic ketimines, providing efficient and highly enantioselective access to valuable benzosultams and benzosulfamidates containing a stereogenic quaternary carbon...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2013-01, Vol.135 (3), p.971-974
Main Authors: Wang, Hui, Jiang, Tao, Xu, Ming-Hua
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Alkenes - chemistry
Amides - chemistry
Carbon - chemistry
Catalysis
Imines - chemistry
Ligands
Models, Molecular
Molecular Structure
Nitriles - chemistry
Organometallic Compounds - chemistry
Rhodium - chemistry
Stereoisomerism
Sulfur - chemistry
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Summary:New, simple, sulfinamide-based branched olefin ligands have been developed and successfully used in Rh-catalyzed asymmetric arylations of cyclic ketimines, providing efficient and highly enantioselective access to valuable benzosultams and benzosulfamidates containing a stereogenic quaternary carbon center. This is the first example of applying a sulfur–olefin ligand in catalytic asymmetric addition of imines.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja3110818