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Issue 2, 2015
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Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides

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Abstract

Stereoselective synthesis of pyrazolidinones via dipolar cycloaddition of azomethine imines with active esters under Lewis base catalysis is presented. The active esters are readily generated in situ from the corresponding acids. Products, which are obtained with excellent diastereocontrol and high enantioselectivity, contain along with the pyrazolidinone core also the tetrahydroisoquinoline structural motif. Theoretical studies give insight into the mechanism of the formal cycloaddition reaction.

Graphical abstract: Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides

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Publication details

The article was received on 27 Aug 2014, accepted on 14 Nov 2014 and first published on 19 Nov 2014


Article type: Edge Article
DOI: 10.1039/C4SC02612H
Citation: Chem. Sci., 2015,6, 1252-1257
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    Stereoselective Lewis base catalyzed formal 1,3-dipolar cycloaddition of azomethine imines with mixed anhydrides

    L. Hesping, A. Biswas, C. G. Daniliuc, C. Mück-Lichtenfeld and A. Studer, Chem. Sci., 2015, 6, 1252
    DOI: 10.1039/C4SC02612H

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