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Issue 47, 2018
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Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates

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Abstract

A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between α,β-unsaturated aldehydes and α-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection.

Graphical abstract: Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates

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Publication details

The article was received on 16 Apr 2018, accepted on 14 May 2018 and first published on 14 May 2018


Article type: Communication
DOI: 10.1039/C8CC03017K
Citation: Chem. Commun., 2018,54, 6040-6043
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    Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates

    J. Sun, F. He, Z. Wang, D. Pan, P. Zheng, C. Mou, Z. Jin and Y. R. Chi, Chem. Commun., 2018, 54, 6040
    DOI: 10.1039/C8CC03017K

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