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Issue 21, 2018
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Asymmetric ring-opening reactions of azabenzonorbornadienes through transfer hydrogenation using secondary amines as hydrogen sources: tuning of absolute configuration by acids

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Abstract

Reductive transfer hydrogenation of bicyclic alkenes has been developed under the co-catalytic system of palladium and silver by using secondary amines as reductants. The reaction results in the asymmetric ring-opening product. A wide range of azabenzonorbornadienes reacted well giving 1,2-dihydronaphthalen-1-amine derivatives in high yields with good enantioselectivities. The control of the absolute configuration of the product by addition of carboxylic acids has been demonstrated.

Graphical abstract: Asymmetric ring-opening reactions of azabenzonorbornadienes through transfer hydrogenation using secondary amines as hydrogen sources: tuning of absolute configuration by acids

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Publication details

The article was received on 29 Dec 2017, accepted on 26 Feb 2018 and first published on 02 May 2018


Article type: Research Article
DOI: 10.1039/C7QO01163F
Citation: Org. Chem. Front., 2018,5, 3077-3082
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    Asymmetric ring-opening reactions of azabenzonorbornadienes through transfer hydrogenation using secondary amines as hydrogen sources: tuning of absolute configuration by acids

    D. Pu, Y. Zhou, F. Yang, G. Shen, Y. Gao, W. Sun, R. Khan and B. Fan, Org. Chem. Front., 2018, 5, 3077
    DOI: 10.1039/C7QO01163F

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