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Palladium/silver co-catalyzed syn-stereoselective asymmetric ring-opening reactions of azabenzonorbornadienes with amides

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Abstract

The first syn-stereoselective generation of 1,2-diamino dihydronaphthalene derivatives by asymmetric ring-opening reaction of azabenzonorbornadienes is reported. Electron-deficient amides have been successfully employed as nucleophiles in the aromatic ring-opening reaction of azabenzonorbornadienes. The reaction was co-catalyzed by Pd(OAc)2 and AgBF4 with (R)-BINAP as the chiral ligand. The ARO products were obtained in good to high yields (up to 96%) with excellent enantioselectivities (up to 98%).

Graphical abstract: Palladium/silver co-catalyzed syn-stereoselective asymmetric ring-opening reactions of azabenzonorbornadienes with amides

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Publication details

The article was received on 10 Jan 2019, accepted on 29 Jan 2019 and first published on 15 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00041K
Citation: Org. Chem. Front., 2019, Advance Article

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    Palladium/silver co-catalyzed syn-stereoselective asymmetric ring-opening reactions of azabenzonorbornadienes with amides

    G. Shen, R. Khan, H. Lv, Y. Yang, X. Zhang, Y. Zhan, Y. Zhou and B. Fan, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00041K

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