Chiral Bicyclic Bridgehead Phosphoramidite (Briphos) Ligands for Asymmetric Rhodium-Catalyzed 1,2-and 1,4-Addition

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A complementary solution for Rh-catalyzed enantioselective 1,2- and 1,4-arylation with two structurally related chiral ligands is reported. A chiral bicyclic bridgehead phosphoramidite (briphos) ligand.derived from 1-aminoindane was efficient for the 1,2-arylation of N-sulfonyl imines, while that derived from 1,2,3,4-tetrahydro-1-naphthylamine was efficient for 1,4-arylation of alpha,beta-unsaturated cyclic ketones. For alpha,beta-unsaturated N-tosyl ketimines, the briphos derived from 1-aminoindane was found to selectively provide gamma,gamma-diaryl N-tosyl enamines with high yields and stereoselectivities
Publisher
AMER CHEMICAL SOC
Issue Date
2016-05
Language
English
Article Type
Article
Keywords

PHOSPHINE-OLEFIN LIGANDS; BIS-SULFOXIDE LIGAND; ARYLBORONIC ACIDS; CONJUGATE ADDITION; DIPYRIDYLPHOSPHINE LIGANDS; REDUCTIVE ELIMINATION; N-TOSYLARYLIMINES; CARBON-CARBON; DIENE LIGANDS; BORONIC ACIDS

Citation

JOURNAL OF ORGANIC CHEMISTRY, v.81, no.9, pp.3520 - 3527

ISSN
0022-3263
DOI
10.1021/acs.joc.6b00033
URI
http://hdl.handle.net/10203/209514
Appears in Collection
CH-Journal Papers(저널논문)
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