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Issue 69, 2014
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Carbonylative enantioselective meso-desymmetrization of cis-epoxides to trans-β-lactones: effect of salen-ligand electronic variation on enantioselectivity

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Abstract

Carbonylation catalysts for the desymmetrization of meso-epoxides yielding enantioenriched trans-β-lactones are reported. Fine-tuning the electronic properties of the ligand further improved enantioselectivity. The sterics of the substrate dictated whether a given electronic variation decreased or increased enantioenrichment, revealing an unexpected relationship between the substrate's steric environment and the electronic nature of the optimal catalyst.

Graphical abstract: Carbonylative enantioselective meso-desymmetrization of cis-epoxides to trans-β-lactones: effect of salen-ligand electronic variation on enantioselectivity

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Publication details

The article was received on 09 Jun 2014, accepted on 05 Jul 2014 and first published on 14 Jul 2014


Article type: Communication
DOI: 10.1039/C4CC04397A
Citation: Chem. Commun., 2014,50, 9842-9845
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    Carbonylative enantioselective meso-desymmetrization of cis-epoxides to trans-β-lactones: effect of salen-ligand electronic variation on enantioselectivity

    M. Mulzer, J. R. Lamb, Z. Nelson and G. W. Coates, Chem. Commun., 2014, 50, 9842
    DOI: 10.1039/C4CC04397A

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