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The hexameric resorcinarene capsule as an artificial enzyme: ruling the regio and stereochemistry of a 1,3-dipolar cycloaddition between nitrones and unsaturated aldehydes

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Abstract

When a 1,3-dipolar cycloaddition between nitrones and α,β-unsaturated aldehydes catalyzed by L-proline derivatives takes place inside the hexameric resorcin[4]arene capsule the products are obtained in higher yields and selectivity, with respect to the reaction in bulk solution. The 4-formyl regioisomers were obtained preferentially, with an excellent preference for the endo-diastereoisomers and with moderate to good enantioselectivities. An extended in silico study was conducted to rationalize the observed outcome and to investigate the equilibria between the reagents outside and inside the capsule.

Graphical abstract: The hexameric resorcinarene capsule as an artificial enzyme: ruling the regio and stereochemistry of a 1,3-dipolar cycloaddition between nitrones and unsaturated aldehydes

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Publication details

The article was received on 16 Oct 2017, accepted on 23 Nov 2017 and first published on 27 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO00942A
Citation: Org. Chem. Front., 2018, Advance Article
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    The hexameric resorcinarene capsule as an artificial enzyme: ruling the regio and stereochemistry of a 1,3-dipolar cycloaddition between nitrones and unsaturated aldehydes

    P. La Manna, M. De Rosa, C. Talotta, C. Gaeta, A. Soriente, G. Floresta, A. Rescifina and P. Neri, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00942A

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