An azo-bridged ring system enabled by-standing immobilization of a chiral diene ligand

A family of 9-azabicyclo[3.3.1]nonadienes were designed, prepared and successfully applied in the rhodium-catalyzed addition of arylboronic acids to N-tosylarylimines, affording chiral diarylmethyl amides with excellent enantioselectivities (up to 97% ee). The nitrogen atom in the bridged ring enabl...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 8; no. 19; pp. 5397 - 5402
Main Authors Xue, Ze-Jian, Lu, Han-Yu, Fu, Jian-Guo, Feng, Chen-Guo, Lin, Guo-Qiang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.10.2021
Royal Society of Chemistry
Subjects
Amides
Catalysis
Catalysts
Chemistry
Chemistry, Organic
Enantiomers
Immobilization
Ligands
Nitrogen
Organic chemistry
Physical Sciences
Rhodium
Science & Technology
Silica
Silicon dioxide
CATALYZED ASYMMETRIC 1,4-ADDITION
BORONIC ACIDS
STEERING LIGANDS
ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
N-TOSYLARYLIMINES
ENANTIOSELECTIVE ARYLATION
CONJUGATE ADDITIONS
ORGANIC FRAMEWORKS
OLEFIN LIGANDS
ARYLBORONIC ACIDS
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Summary:A family of 9-azabicyclo[3.3.1]nonadienes were designed, prepared and successfully applied in the rhodium-catalyzed addition of arylboronic acids to N-tosylarylimines, affording chiral diarylmethyl amides with excellent enantioselectivities (up to 97% ee). The nitrogen atom in the bridged ring enabled a facile immobilization of diene ligands to silica. The obtained heterogeneous catalyst was evaluated in the above addition reaction and reused five times without significant loss in yield and enantioselectivity.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d1qo00852h