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Pd-Catalyzed Asymmetric Allylic Substitution Cascade via An Asymmetric Desymmetrization for the Synthesis of Bicyclic Dihydrofurans

Abstract

A Pd-catalyzed asymmetric allylic substitution cascade of allylic meso-dicarbonates with 3-oxo-nitriles has been developed for the synthesis of chiral bicyclic dihydrofurans bearing two vicinal carbon stereocenters. The reaction proceeds via an asymmetric desymmetrization process with the desired products being obtained in high yields and with up to 97% ee. The reaction was performed on a gram-scale and the corresponding bicyclic dihydrofurans could undergo several transformations. The methodology provides an efficient synthetic route to biologically active chiral bicyclic dihy-drofurans derivatives.

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Publication details

The article was received on 16 Sep 2019, accepted on 11 Oct 2019 and first published on 11 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC07204G
Chem. Commun., 2019, Accepted Manuscript

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    Pd-Catalyzed Asymmetric Allylic Substitution Cascade via An Asymmetric Desymmetrization for the Synthesis of Bicyclic Dihydrofurans

    K. Xu, H. Liu, Y. Hou, J. Shen, D. Liu and W. Zhang, Chem. Commun., 2019, Accepted Manuscript , DOI: 10.1039/C9CC07204G

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