Rhodium-Catalyzed Asymmetric 1,4-Addition of alpha,beta-Unsaturated Imino Esters Using Chiral Bicyclic Bridgehead Phosphoramidite Ligands

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A chiral bicyclic bridgehead phosphoramidite (briphos) prepared from 1-aminoindane is a highly efficient and selective ligand for rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to alpha,beta-unsaturated N,N-dimethyl-sulfamoyl imino esters at ambient temperature. This transformation provides a new class of chiral (Z)-gamma,gamma-diaryl-alpha,beta-dehydroamino esters with excellent yield and enantioselectivity.
Publisher
AMER CHEMICAL SOC
Issue Date
2015-09
Language
English
Article Type
Article
Keywords

PHOSPHINE-OLEFIN LIGANDS; BIS-SULFOXIDE LIGAND; ARYLBORONIC ACIDS; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; DIENE LIGANDS; BORONIC ACIDS; ALKENYLBORONIC ACIDS; N-TOSYLARYLIMINES; ALPHA-KETOESTERS

Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.137, no.35, pp.11250 - 11253

ISSN
0002-7863
DOI
10.1021/jacs.5b07034
URI
http://hdl.handle.net/10203/205366
Appears in Collection
CH-Journal Papers(저널논문)
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